and most of the time is  bad management, bought the wrong price, Interest and Insurance to the roof and, I cant get out the Bridge loan to do a DSCR loan etc ...Simple hands on, work do research and minimize risk. 

Have you ever had a client or partner misunderstand 100% financing and expect it to cover closing costs?

Rent paid for all of the expenses, so it cost me nothing and over the years (I kept it for ~20 years) price almost tripled by the time I sold it.Not sure what grad program is 3 years (I'm used to 2 for masters, 4 for PhD), but if you do need to sell one, I'd look at each property and see which one has the most equity, highest interest rates, lowest return, major expenses in the near future (eg new roof) and you mentioned you'd lived in two for 2 of the last 5 years, so have capital gains exemptions. 

I could write a whole book about STRs, and it still will not cover everything, because...Take-home 2: tax strategies are always case-by-case, there's no universal recipe, which is why...Take-home 3: use a good tax professional, such as those listed here: https://www.biggerpockets.com/...

The roof is fine until it leaks, decks are fine until they are not, things wear out, line blockages don't happen overnight they most often are buildups over time until the result IS seen overnight. 

Everyone needs a roof over there head.

Outside of real estate I am in the construction industry, in Commercial / Residential Roofing.

My wife and I have our old primary home that we recently moved out of and are renting that has 150K+ in equity that we could tap into via HELOC to fund the down payment for our next purchase and cover the remainder with a DCSR or Conventional loan?

if so - are you wanting to borrow just  enough to pay off the loan and cover refi costs  or  are you wanting to pull out more funds over and above the loan balance ? 

The Federal Americans with Disabilities Act and the Federal Fair Housing Act approach the topic differently and cover different segments of the community.