But occasionally we have issues and tenants need to be asked to leave or just decide to disappear in the middle of winter and it sucks.The worst part is I find the quality of tenant interested or willing to move this time of year isn't the greatest either - often times there is a reason they have to move right now since most landlords don't like ending leases this time of year.Either lower your rent or just hang in there.

Consult with competent legal counsel to guide you regardless of your choice here.

I think that's a great approach I have a lot of clients who self manage have no issues at all.  

It does however give you a degree of independence to choose what you want to do.As your portfolio grows you'll also feel the weight of future capex responsibility more, which ironically points you to growing more cash flow through more real estate.The other issue is that you are chasing a moving goalpost.

If that's your only issue, then you should be OK. 

You can sell a property with tenants with no issues the only thing is you wont see as good of a price for the property since it will likely be an investor purchasing it.

I don't foresee any issues but I'll keep you posted.

Buying through an agent may provide more transparency, while sheriff sales and auctions can offer deals but often come with risks, like limited property inspection or legal complications.

There i a bit of research that needs to be completed early on in order to get a good judgement on the feasibility of this; from there, the "Official" way to ensure you could pursue this would be to request a "Zoning Opinion Letter" to receive an Official decision from the Department of Zoning in order to ensure this will not cause any issues during your permit review. 

I keep reading about all the weird financing issues in this space so I wouldn't actually put money in until mid 2025 or later.