Often times, they just forgot it’s the first of the month (though now with automatic payments via Cozy, that rarely happens).

Not a shock (masons are *extremely* busy, so they're not exactly looking for business)Contacted two other masons (one via YELP referral, one through personal connections). 

The reason I'm researching this avenue is despite saving for 5-10 years via conventional retirement vehicles, I've come to the conclusion that without some further active action by myself I won't be able to live the same lifestyle I currently live in retirement.

THAT is how people elevate themselves NOT via handouts, your "donating" is propagating the problem. 

Just buy, pay through personal bank, and then reimburse self via business checking to personal checking.

Conventional mortgages are capped at 10, and I think 4 via one bank.

That can be via a vetted buyer's list, REI contacts, family, but you have to know you can close these deals on assignment that you agree to buy just in case you can't find the right buyer.

If you're house is worth around $390k and you are going to spend $150k on an investment, I'd pay cash via your heloc and refi in to a 30 year fixed as soon as it's seasoned and pay off the HELOC, then start the process all over.

Send me your email via DM and I'll hit you up, currently on leave in the states.  

Unload this property now via sale or 1031 exchange and look for a new investment2.