Temperature control:  It's always naturally cooler downstairs, and in the heights of summer and winter, I just cannot get the temperature regulated for both me and my tenant to where we're both comfortable. 

Byzantine planning and landlording regulations.

Consider exploring financing options like FHA loans or conventional loans with low down payments, understanding local regulations, and conducting market research to ensure you can cover your costs.

@Jeremy D.2nd kitchen and you would need an ADU license, and of course needs to meet the adu requirements.An adu is not multifamily, so yeah cant have the 2 parts rented seperatly when you leave.Whats unclear as I dont think its adressed in the regulations, is if you have an ADU, would 5 persons be the total property limit.

Trump did not address housing as directly but has previously suggested cutting regulations and using federal land for new construction.Sharing this because it could have a significant impact on the housing market in the near and long term. 

Structural and Foundation issues can really slow things down because the municipality will get involved with all their procedures and what not what it comes to those two areas. 

Here are 2 articles talking about new regulations they're trying to put on STRs there, which definitely could impact your rental income, especially if you buy in an R-1 area. 

I just can't see a world where there isn't some tax change that happens next year to at least make some of the more procedural items of the TCJA permanent + other changes.

Yes, it is possible, but the procedure is indeed confusing, and even we tax professionals, myself included, have made incorrect statements.It sounds like you have already filed your 2023 tax return.

Compliance issues regarding local landlord regulations not an issue in my area.