I actually tried Cherif Medawar's program and have found Licensing Experts vastly superior in a couple of ways. 

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

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).

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

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.

Based on what did end up in the house, she spent very little on actual decor for the house.