If they are priced decent it's very competitive once it hits the timeframe for investors to write an offer and as others have stated the contracts are not assignable.

I also had a tenant that dressed in expensive Italian suits every day.

While health insurance is never inexpensive, the high deductible of HDHPs means lower premiums (pay the small stuff out of pocket and use the HDHP as catastrophic insurance for the big stuff).HSAs have some great tax benefits and the trustee can be anyone already approved by the IRS to be a trustee of IRAs.

We have thought about pulling the trigger up there because its so inexpensive.

So overall I couldn’t really give you a accurate time frame on that. 

I never really expected this to be a cheap or easy project.Marketing and name presence are substantially more problematic from what I can see, because at the end of the day, HA/VRBO & Airbnb have spent a lot of time and money to develop it, and I can't really expect to have anything that can compare to that in a reasonable time frame.

If it's going to book whether or not you take the booking for most of that timeframe anyway, I would just charge them whatever it is to book for everyday in that period and maybe offer some small discount (like 5% per night). 

The rest of the features can be used to adjust the price.If there's not enough data, it's better to push out the sold time frame than to push out the search radius.  

I'd start doing simple, inexpensive things to create equity in your properties- paint, carpet, updated light fixtures, etc.

It’s fast, easy, and relatively inexpensive to reach target audiences.