I dont think he will ever pick them up since he is a travel worker and already out of state.

And then (or step 1 if you already own.) find a friend/relative/co-worker, or two you like to rent a room from you. 2 people paying $750/mo each is pretty close to your goal in one step.If you rent or the thing you own is too small to do that get your friend to help you fix up a “dump” you can get cheap but feel comfortable living in day 1.

A mid-term rental could be an great option during the 6-7 months you're away since it appeals to traveling professionals, remote workers, or individuals relocating and offers stable income without the constant turnover of short-term rentals.

It's probably being done in an illegal fashion from the way you describe it.

–Exception: An ADU on a 1-unit subject property that does not comply with the zoning and land-use requirements (illegal zoning) may be eligible under certain conditions. • ADUs that are manufactured homes are allowed under certain conditions.Good luck

•Mid-term rentals (30+ day stays) can be another fallback option, especially for traveling nurses, corporate workers, and digital nomads.5.

Seasonal workers, ski guides, raft guides, restaurant staff, etc. 

Lower acquisition costs than urban markets, steady demand from families and remote workers, and less competition than SFH-heavy suburbs.

This week, the City of Jacksonville Municipal Court ruled in favor of PadSplit, voiding citations for "illegal boarding houses" on constitutional and fair housing grounds.This marks a huge victory in expanding affordable housing solutions while navigating legal challenges.

Or if they continue to be difficult to work with, start looking for a new property manager.I don't think it's necessary for you to specifically mention in your listing description that you accept section 8 tenants because it's illegal to discriminate on the basis of income in Illinois, which protects Section 8 voucher holders.