and are guests mostly short term or mid term? 

I’m about 4 years from retirement and regretting not venturing into this world sooner.I’m currently going back and forth on whether to focus on short term rentals in Florida (Destin, PCB) or long-term single family homes in the Birmingham, Al area.

I have a great tenant.... ....she will be $900 short on rent this month and she says it is getting harder to pay every month.....She has never been late or given issues....

This can be a problem if you wait to get your new property under contract after the closing of your sale.   

Ask them for a copy of their purchase agreement and have it reviewed by attorney to see if the terms are acceptable to you.5.

I am eager to build long-term, mutually beneficial relationships with wholesalers who can provide quality properties that meet our criteria.If you are a wholesaler in the Cleveland area or its suburbs, or if you have any recommendations, I would love to hear from you.Please feel free to reach out to me via private message or respond to this thread with your contact information and a brief overview of your offerings.Thank you for your time, and I look forward to the opportunity to collaborate with some of the fantastic wholesalers in our community.Best regards,Tom. 

Long-Term Vision: Sure, the duplex is step one, but what’s my long-term game plan?

You can make the contract contingent upon basically anything.

If you're dead set on self-managing, find and purchase a property that already has long-term tenants and will want to stay after the turnover.

I have a long term tenant that seems to state that they’re having ants, spider, and wasp problems.