This is a question that really cannot be answered in one post.

@Michael Plaks is spot on - character wise, 1099-R income falls in the same "bucket" as a W-2 wage would be, thus to offset this income with real estate losses, it follows the exact same pathway (ST rental with material participation or REP status with traditional rentals), but since you don't have all your time sucked up with a W-2 job, you have much greater flexibility to hit those related hours thresholds under those paths as well.No idea if he's taking clients - but if you are looking for local(ish) and qualified in TX, Michael is also likely a great one to reach out to.

Each time I work with my bank to get a new HELOC at a higher amount, it takes the place of the old one and assumes it's balance, however I now have more to draw from to continue investing.

You also cite that you need one that will track all your expenses easily.

The strategy that works very well is they use their VA loans to buy a 2-4 unit property, and live in one unit and rent out the rest.

@Lindsey Bodner, One thing I believe you may be mistaken about is that the payments are not made to you.

First one would be Zillow Rooms - in terms of range and scope of audience.If you want to be formal and have great photos then try on coliving.com Also I believe that booking.com allows it. 

I'm not a big fan of one beds, and the commercial has to be underwritten at higher cap rate than the commercial.Historic sounds like a lot of deferred maintenance.

I specifically know one that goes up to 90% CLTV

But if you want the best value for your real estate training Paul McGraw’s program is the best one I’ve tried and I’ve tried Carlton Sheets, Robert Kiyosaki, ************* and a few others I don’t remember over the years.