There's a lot of options out there for you but you'll definitely want expert advice to help you navigate the nuances of the laws.  

I would like to learn more about how lenders view the following situation and how to best navigate the process:Say I have a property (that I live in) that I purchased with a 5% down conventional loan.

During my time in Enid, I will be in pilot training which is a pretty rigorous training program.

The reason I suggest a broker is because you really need somebody who knows how to navigate the conventional Fannie/Freddie guidelines along with understanding the non-warrantable portfolio products.

Your time here will be well spent.Since your primary focus is on rentals I added the below links for your review.https://www.biggerpockets.com/renewsblog/2015/05/26/real-estate-financing/ (RE financing)https://www.biggerpockets.com/renewsblog/2015/03/27/financing-options-rental-property-guide/ (financing options for rentals)https://www.biggerpockets.com/renewsblog/2014/03/06/bp-podcast-060-serge-shukhat/ (0-68 rentals in 4 years) https://www.biggerpockets.com/renewsblog/2014/08/02/passive-real-estate-investing/ (slowly building wealth through passive investing)https://www.biggerpockets.com/renewsblog/2015/09/30/bought-rehabbed-rented-refinanced-14-properties/ (BRRRR explained)http://www.biggerpockets.com/renewsblog/2013/01/04/how-to-rent-your-house/ (house rental guide)http://www.biggerpockets.com/renewsblog/2013/02/22/buying-rental-property/ (how to buy a rental property)Now that you have made the move, below are some links that will help with the navigation of the site. http://www.biggerpockets.com/startherehttp://www.biggerpockets.com/meethttps://www.biggerpockets.com/alertsHow to Use @Mentions on BiggerPocketshttps://www.biggerpockets.com/ruleshttps://www.biggerpockets.com/termshttps://www.biggerpockets.com/inviteshttps://www.biggerpockets.com/perkshttps://www.biggerpockets.com/forums/categorieshttps://www.biggerpockets.com/rei/glossary/https://www.biggerpockets.com/courses/a-beginners-introduction-to-real-estate-investing (video courses)https://www.biggerpockets.com/real-estate-investing (Ultimate beginner's guide to REI)Before your 1st purchase, please ensure you visit the below link for some tips.https://www.biggerpockets.com/renewsblog/2014/12/19/real-estate-investing-success-smart-tips/REI books suggested by BPershttps://www.biggerpockets.com/renewsblog/2015/11/13/7-real-estate-books-beginner-investors/ (7 absolute must read books for beginner REIs)http://www.biggerpockets.com/renewsblog/2013/04/14/best-real-estate-books/?

I received this info from @Nathan Sharp when I first started.https://www.biggerpockets.com/renewsblog/2013/11/02/hack-housing-get-paid-live-free/ (House hacking)https://www.biggerpockets.com/renewsblog/2014/03/13/investing-multifamily-ben-leybovich/ (Podcast 061 - How to succeed in multifamily investing)https://www.biggerpockets.com/renewsblog/2013/04/09/how-to-buy-a-small-multifamily-property/ (How to buy a small multifamily property)https://www.biggerpockets.com/renewsblog/2015/11/16/how-to-choose-areas-multifamily-deals/ (Choosing multi-family deals)http://www.biggerpockets.com/renewsblog/2014/07/19/how-to-buy-a-duplex/(guide to buying a duplex)https://www.biggerpockets.com/renewsblog/2013/12/12/bp-podcast-048-duplex-managing-tenants-darren-sager/ (Duplex investing)Now that you have made the move, below are some links that will help with the navigation of the site. http://www.biggerpockets.com/startherehttp://www.biggerpockets.com/meethttps://www.biggerpockets.com/alertsHow to Use @Mentions on BiggerPocketshttps://www.biggerpockets.com/ruleshttps://www.biggerpockets.com/termshttps://www.biggerpockets.com/inviteshttps://www.biggerpockets.com/perkshttps://www.biggerpockets.com/forums/categorieshttps://www.biggerpockets.com/rei/glossary/https://www.biggerpockets.com/webinarhttps://www.biggerpockets.com/courses/a-beginners-introduction-to-real-estate-investing (video courses)https://www.biggerpockets.com/real-estate-investing (Ultimate beginner's guide to REI)Before your 1st purchase, please ensure you visit the below link for some tips.https://www.biggerpockets.com/renewsblog/2014/12/19/real-estate-investing-success-smart-tips/REI books suggested by BPershttps://www.biggerpockets.com/renewsblog/2015/11/13/7-real-estate-books-beginner-investors/ (7 absolute must read books for beginner REIs)http://www.biggerpockets.com/renewsblog/2013/04/14/best-real-estate-books/?

I received this info from @Nathan Sharp when I first started.http://www.biggerpockets.com/renewsblog/2013/01/04/how-to-rent-your-house/(house rental guide)http://www.biggerpockets.com/renewsblog/2013/02/22/buying-rental-property/(how to buy a rental property)https://www.biggerpockets.com/renewsblog/2013/11/02/hack-housing-get-paid-live-free/ (House hacking)https://www.biggerpockets.com/renewsblog/2014/03/13/investing-multifamily-ben-leybovich/ (Podcast 061 - How to succeed in multifamily investing)https://www.biggerpockets.com/renewsblog/2013/04/09/how-to-buy-a-small-multifamily-property/ (How to buy a small multifamily property)https://www.biggerpockets.com/renewsblog/2015/11/16/how-to-choose-areas-multifamily-deals/ (Choosing multi-family deals)http://www.biggerpockets.com/renewsblog/2014/07/19/how-to-buy-a-duplex/(guide to buying a duplex)https://www.biggerpockets.com/renewsblog/2013/12/12/bp-podcast-048-duplex-managing-tenants-darren-sager/ (Duplex investing)Now that you have made the move, below are some links that will help with the navigation of the site. http://www.biggerpockets.com/startherehttp://www.biggerpockets.com/meethttps://www.biggerpockets.com/alertsHow to Use @Mentions on BiggerPocketshttps://www.biggerpockets.com/ruleshttps://www.biggerpockets.com/termshttps://www.biggerpockets.com/inviteshttps://www.biggerpockets.com/perkshttps://www.biggerpockets.com/forums/categorieshttps://www.biggerpockets.com/rei/glossary/https://www.biggerpockets.com/webinarhttps://www.biggerpockets.com/courses/a-beginners-introduction-to-real-estate-investing (video courses)https://www.biggerpockets.com/real-estate-investing (Ultimate beginner's guide to REI)Before your 1st purchase, please ensure you visit the below link for some tips.https://www.biggerpockets.com/renewsblog/2014/12/19/real-estate-investing-success-smart-tips/REI books suggested by BPershttps://www.biggerpockets.com/renewsblog/2015/11/13/7-real-estate-books-beginner-investors/ (7 absolute must read books for beginner REIs)http://www.biggerpockets.com/renewsblog/2013/04/14/best-real-estate-books/?

Your time here will be well spent.I added the below wholesale guide for your review as a result of your interest in this niche.https://www.biggerpockets.com/renewsblog/2015/01/31/ultimate-beginners-guide-real-estate-wholesaling-2/ (Ultimate beginners guide to wholesaling)Now that you have made the move, below are some links that will help with the navigation of the site. http://www.biggerpockets.com/startherehttp://www.biggerpockets.com/meethttps://www.biggerpockets.com/alertsHow to Use @Mentions on BiggerPocketshttps://www.biggerpockets.com/ruleshttps://www.biggerpockets.com/termshttps://www.biggerpockets.com/inviteshttps://www.biggerpockets.com/forums/categorieshttps://www.biggerpockets.com/courses/a-beginners-introduction-to-real-estate-investing (video courses)https://www.biggerpockets.com/real-estate-investing (Ultimate beginner's guide to REI)Before your 1st purchase, please ensure you visit the below link for some tips.https://www.biggerpockets.com/renewsblog/2014/12/19/real-estate-investing-success-smart-tips/REI books suggested by BPershttps://www.biggerpockets.com/renewsblog/2015/11/13/7-real-estate-books-beginner-investors/ (7 absolute must read books for beginner REIs)http://www.biggerpockets.com/renewsblog/2013/04/14/best-real-estate-books/?

how do i navigate this?

a place to start with site tour would be good. might be an idea to emphasize please read the rules as they are different from many other sites and the internet is changing. it is a shock to most creative types, the rules sites come with these days (no kidding), esp for those who have been on the net since the beginning and seen drastic swings and changes in regards to rules and etiquette. one minute everyone is stealing mp3s and not paying artists, and now you can't post anywhere twice or you get deleted (many sites now). very difficult to navigate.