A lot of "professional tenants" know how to work the system, and know all the tricks to play to prolong eviction.

Scott, just didn't say it, sounds like the contractor is playing you, I hate that.I try to have a little conversation with a new contractor in asking for any bid.I'll mention I'm in the business, I give a general scope of work, in doing that I mention some of the steps involved, just to let them know I know.

I take it you had this scenario play out by the way you were explaining things?

To play devils advocate for a moment, to the mentor program, you asked and they said you could speak to another client.

I've thought about turning it into a small park/playground so she'll have it to play at as she grows.

I've been involved in the vacation rental business for 20 years and have bought/sold seven of my own properties in the last ten.One word jumped out at me from your post - 'emotion' - and I'd advise removing that as much as possible from any buying decision when looking at purchase that involves a vacation rental goal.Of course, your own criteria comes into play because you want to use the place yourself, and you have experience with visiting the area, but you should also consider the needs, wants and desires of your potential guests.

I feel like I'm playing Monopoly, haha.

Anyone who plays an alto sax should have some space around them, unless it's a commune of musicians!

This deal is thin,$5K in repairs,equity is too thin,rent spread is too thin, Possible play: get an option to purchase via sub 2, record the option, sell the option to your investor buyer.

By the way, I read your blog post about playing to your strengths as an investor and really enjoyed it.