For years they made bank as a pioneer in the STR market.

I realize its one of the priciest markets in the US.Any thoughts I'd like to keep it a couple hundred thousand for the lot.

Now there are tertiary markets in the US that will be low value assets but not super high risk those are your smaller towns but your upside is severely limited.

For direct booking, Boostly is a solid option.As you grow, consider integrating mid-term rental marketing for steady income with 2-3x the rent, as well as less turnover and wear.

She'll pay me market rate rent, thus keeping that money in the family, and the condo will eventually transition into a more traditional rental property that will support my retirement and that my children will one day inherit. 

Each of those should know each other in a market as well.One thing to be aware as an out of state investor is that there are unfortunately people out there to take advantage.

(Note: I did not factor Vacancy/Maintenance/etc yet)*Both tenants pay utilities currently but I still factored in water/sewer monthly @ $150 ( See Linked Report)Realtor states current rents should be closer to $1,500 each side to match the market. 

For example, I have a duplex that I tried to sell off market through Facebook Groups.

These properties include different foreclosures and those that sell below their market value.

Quote from @Peter Tverdov: Think at least for the text standpoint it is challenging in this market now where I know personally 3 people that have been in lawsuits with one ringing in at $500,000 for cold text messages to people that did not want to be marketed to, so to @Jonathan Greene point on that for sure.I think that cold calling is a true skill that really no one (or 1%) will end up doing, and I 100% agree that VAs do not do it right..