I'm also putting away money into 401k (roth) from my job as it's giving away free money matching.Unfortunately the support from work is not giving me adequate tools to plan my future considering my real estate and my goals.My plan is to keep the real estate until i can suck out all the depreciation (or most) then exchange like-kind property to not have to pay that money back.

There needn't be a 'ton' of equity, simply enough to support an appraisal of the asset that allows one to refinance their entire investment out.

Some admit they 'worked off the books' to avoid child support, others just had no clue how to take advantage of the many tax deferral plans or appreciate the advantage of Social security later in life as most have nothing saved. 

Section 8 is support that is attached to the tenant, not the house. 

They have more skin in the game then you do.Make sure you get clear title.

They have conservative leverage, put high skin the game, have been through multiple real estate cycles with no investor money lost and have very favorable tax treatment.

You want to find a location that will support the use/uses of real estate for a very very long time - hundreds of years. 

Purchase a home with $30,000 down but give them $15,000 in December 2020 and $15,000 in January so you don't exceed the annual gift contribution.If you're going to do it, I'm sure there are plenty of ways to skin that cat without Uncle Sam stealing the hide.

I am sorry for such a low level stump so to speak, but I am torn on this and my network of support is lacking since I haven’t put the work into building it.

Cut rents.If you decide to invest in a market where Govt forces are already meddling with the free market substantially, be prepared to get skinned alive is all I can suggest.