We can talk about that more in detail because it can be a long conversation, but it depends on you, your palat for risk, and the numbers that make sense for you as an investor. 

But was this cash out refi a bad choice regardless of circumstance as I depended on that money and it was already making money (and was paid off)...now I have a mortgage and make significantly less money per month.

@Lincoln Selk depending on location that isn't a very good deal.

Account Closed - so much of the question about tenants is going to be dependent on the class of property you are buying...Vacancies - I run about 7-8%City - if you have a code violation they give you plenty of opportunities to fix.

., Some depends on their attitude and intent in owning the condo.  

It's great to have the business protection, but depending on what state you're in and how much it costs, you may want to see if real estate investing is really for you first.  

Just depends on what you want to invest in.

Answers to your question would be highly dependent on whether or not you plan to continue buying more rentals, continue flipping, etc.  

Investing in a REIT will give you a lower rate of return than a well bought multiunit - house hacking is the easiest way to get in with that amount of capital - otherwise, you need more than that for the down payment - depending on prices in your area.

It depends a lot on how much that initial rehab is. $5K on a 4plex isn't very much at all.