Look at their marketing strategy.

Step #PhaseStep1DiscoveryTalk to experts and learn (process, tips, design tips)2DiscoveryCreate social media and document story3DiscoveryGeneral research - budget considerations, financing options, permits, regulations, tax considerations4DiscoveryMarket research - competitor analysis, analyze guest reviews, market trends5DiscoveryGather ideas/inspo (blogs, articles, youtube)6DefineCreate brand and vision7DefineCreate guest requirements (e.g. coffee maker, natural light, near activities, etc.) and prioritize must have, nice to have, etc.8DefineSketch idea for look and feel (architecture and design) - map out the floor layout9DefineConsult an architect (is this needed?)

What markets are you looking at for STRs?

It has been 6 months or so, and I want to get them on a lease, and adjust the rent for market conditions.They currently pay $1,500/month, market for this small house is $2,200 or more

So I looked at some local markets like Sacramento where I'm from and familiar with the neighborhoods but the cashflow would be so negative that I'd be paying out of pocket every month.Now I'm more inclined to buy a single family in KC as it seems the rates won't drop anytime soon so would like to get in the investment game sooner than later and hope for a rate drop in few years to refinance.I have been looking on Zillow, and recently connected to an agent to run numbers and seems I could make about $100-$300 after mortgage payment and insurance.

Here in Chicago (Illinois) you can only wholesale (market for sale) one property per year without having your real estate license.

of course you have to handle the inquiries… but it’s pretty easy… we’ve done it multiple times.Your 6% appreciation approximation is less than the 7% average return the stock market  does long term - and lately it has been blowing that figure away - though as they say - past performance doesn’t equal future performance. 

Try to get her out, use the deposit to turn the property around, and try to find a new renter quickly.One suggestion: I would only forgive the July rent if she works with you to market and show the property to new applicants.

I know the process of touring houses, getting home inspection, researching market rents, looking for tenants, screening tenants, etc takes up a lot of time.

Also, Days On Market (DOM) are up across the USA.