It helps the GC to have an idea of what you want to do, so yes, if you want to spend money on an architect to do a conceptual site plan and a civil engineer for site improvement plans, you could do that.

I’ll work on improving his presentation, confidence, and charisma (Lord help me, lol).

https://www.clevelandohio.gov/city-hall/departments/building...A few properties are still registered, you can check them here: https://aca-prod.accela.com/COC/Default.aspxIs this an intelligent method of getting a rental registration and improving the city?

For whatever it is worth, we rent our STR by the month during the non-tourist season and we have a walk-through video on YouTube.

However, if the renovation significantly improved or upgraded the property, you might need to capitalize it as an improvement, depreciating it over 27.5 years.If this was STR, you could write off the improvement under bonus depreciation as well.

If your unit is more B/C class where you can attract lots of decent hard working entry level to middle class workers then I would focus on improving the units to capture those kinds of tenants and oust the trouble makers you have. 

Still learning a lot as we continue to grow and improve. 

If they stay more than five days, I recommend treating it somewhere during their stay.There are a lot of guides on youtube or Google specific to short-term rentals.

Check out Erin Spradlin on YouTube 

You can influence your investment's performance through property improvements, rent adjustments, and savvy management... something you can't quite do with an annuity tied to obscure indexes.An Individual Retirement Account (IRA), particularly a Self-Directed IRA, can be used to invest in real estate and employ leverage to potentially enhance returns.