Boddie-Noell Enterprises, Inc. v.

Potentially, if you do not secure your priority by purchasing all the subsequent liens, even forcing the APR down to 1% or 2%, you could run the risk of the property selling at foreclosure and not paying off your tax lien from three years ago.Tax liens will require a good amount of liquid capital to be held for the purpose of foreclosing and winning your already "tax lien" owned property.

Subsequently, the property manager placed a Stop Order on the previously issued check covering the portion of the security deposit that was not in dispute (the tenant had not yet cashed the check).  

If you are going to new Private Money Investors you can set the tone with the initial offer as they may not have considered what terms they are really looking for.I would go for Structure 2 with 8-10% interest to make it juicier for them - no one is going to get too excited over 5-6% and with the numbers you are showing you can cover the extra few percent.If you perform over time you can get better terms with subsequent loans from private lenders a lot of times.

This is human nature.When I was starting out in my career, I believed that engaging in commercial enterprise was vulgar and best left to company management.

A short term rental is a commercial enterprise. 

As your enterprise expands, consider engaging an impartial third party to conduct periodic assessments.

Many PMs don't want to handle the area at all, because the rents aren't so high and subsequently they're percentage isn't that high.

I definitely wouldn't say that I have analysis paralysis, but I do want to fine-tune my exact vision and then commit to offering on everything that meets my subsequent buying criteria. 

For example buying in 2006 was a poor time to buy and buying in the subsequent 6 years in virtually all markets, and some markets much longer, would be better.