15 - 20 year hold time.The rental investment calculators show that the four $300k properties would have a lot more equity in the future and many times the cash flow after a few years, but does the extra maintenance, management time and expense, etc. outweigh the numbers?

I know it seems like a tough task, but can you spend a few more months or a year while you continue to learn to really tighten the budget or find ways to earn a little extra to start from a stronger position?

We all know what goes on in bathrooms and what kind of extra care they need.

Adding in the layer of not being on the loan but holding title just sounds like it will eventually lead to problems like OP experienced.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

Like maybe I could pull enough out from heloc on primary residence to pay off debt and then rent out my primary and use the extra cash to payoff heloc and then do another heloc once the original one is paid off.

Finally, of the extra $200k, how much are you putting into operating reserves? 

Knowing cap-x projected out years is not an "extra credit" kind of information, it's fundamental necessity. 

(I’m ignoring any extra cap-x because you said it was a condo, but you’d also add any major cap-x to cost basis).

//End extra detailsI say all that to illustrate how much he seems to thrive on conflict.