I am happy to say that I have earned WAY more $$$ in return than the initial investment of joining the community and am set to retire in the Summer of 2023 from the military.

This is a great forum with very knowledgeable members that will help to guide you in the right direction.I really like the alerts feature that can quickly guide you to current topics that might interest you: http://www.biggerpockets.com/alertsIf you are looking to connect with other members near you, or want to learn from people in a specific area you’d like to invest in, or have a desire to find people interested in certain topics, you could start your search here: https://www.biggerpockets.com/search/users

This makes property more desirable for resale if investors have more flexibility in what can happen tenants.  

Good morning Michael,For a faster and smoother sale where you can earn top dollar for the property, I'd recommend selling vacant.If you prefer to keep the tenants in place and sell "as-is", you will have to sell at a number that makes sense to a rental property investor in that market.

Looking to see if anyone that's invested in Milwaukee has any insight in terms of finding contractors to work in less desirable areas.

Not to mention the purchase price is much lower which would allow my capital to be spread a tad bit further.Thankfully, since I still hold my license, I can use the commissions earned as well to cushion some of the downpayment/reserves needed upon closing.My questions are below and I would appreciate any/all feedback for those who buy/hold affordable housing/section 8:1.)

Most of what I have seen on Zillow/Realtor/Redfin has been in the so-so parts of town with the occasional fixer upper closer to the more desirable areas. 

I need to compare the profitability as well as tax ramifications for two options I’m grappling with. we currently own a home in which the tenant is in a lease w/ an option to purchase -but the contract is coming to an end soon and she does not have the ability to purchase the home/get a conventional loan yet- but desires to work toward that.

I realize that I may be limiting myself to less desirable properties by not accepting a higher monthly mortgage.

You can partner with them or become a lender on their deal and earn 8,10,12 % while hopefully learning from them.