Keep in mind that my plan for my first property is to find a property that has a guest house of some sort detached from the main property.

Have a 'if you were in my shoes as an investor, what things would you keep in mind' sort of conversation, so you can get a sense as to whether or not you're on the same page and if this is someone you want to do business with...... 

Hey Chris, for the most part i been online lately, my marketing has either been done by Bandit Signs, direct mail, dropcards, and i had lil bit success in the past but back then my mind wasn't clear on things like it is now and i refuse to door knock especially in the area im in, i tried it before it's not many owners motivated to sell, around my way is lack of owners just mostly people that are renting a property.

You can ask your agent, but they probably won't give be able to you super specific information unless you already have an area in mind.

Looking at them struggling to answer my questions gets my double minded whether to move further or not.

@Austin Hendrickson ...yea  If you read (c) For the special rules as of right now (keeping in mind that it may change in the future...)but it specifically states "any investment" held by the taxpayer. 

Another item to keep in mind is that, in many states, in addition to the "homestead protection" mentioned above, most types of retirement accounts are also protected in lawsuits. 

Change your mind set. 

Do you mind sharing the interest rate your paying with that HML currently?

@Ilmar Molderg i live in houston and invest in CT and manage everything myself. however i certainly respect that you want a manager and also someone to find and calculate deals. to be honest, yes you’re sort of right that someone may just keep the deals for themselves. i guess what comes to mind is that you need to find a really good agent that is familiar with investments and also a really good wholesaler. both of those people are fully capable of running numbers for you and helping you like you’ve described. i invest in the central CT area but may be able to refer someone to you.