There was no one in tech support I could actually chat with.

I actually am an attorney, and still send mine for extra vetting. 

When I asked what happened with the applicant, they took weeks to inform me that squatters had moved into the property. 3) When I asked for a copy of the court paperwork they had filed (to ensure they were actually doing something about it and to discuss with my own lawyer), they reassured me vaguely they were taking steps while they moved slowly without telling me what exactly they were doing.

And we've got a mall that hd a huge Macy's or maybe it was saks 5th ave I can't remember, regardless they through a huge volleyball facility in the space and that has really been driving the mall, its actually really cool, they left a huge window into the rest of the mall so people can see in walking buy...very well thought out.

When you do that, you can get better pricing and leaves less room for error.The best advice is to push forward as quick as possible, fail forward, and always continue to introspect on what you would do differently and then ACTUALLY go back and implement that change (easier to say than do).

He was happy to allow me to rent out nightly because it actually helps keep his property in better shape than a long term renter (having a cleaner in there every turnover, short stay guests always let you know when something isn't working, etc) but didn't want to hassle with worrying about a percentage of income/management, etc.

If you added in the cash you should have to protect against contingencies, the actual return goes down (or the risk sykrockets, your choice)- If the $300K properties cashflow, definitely a better bet. 

My lot is actually only 75' wide but was grandfathered into the zoning once they made the setback changes (neighborhood is late 1950 builds). 

It simply depends on your time frame, when you want to actually begin renting the property out short term, and what the loan terms are.

It will help a lot if you understand accounting and how the statements are actually generated.