If the HOA seems like they’re making things tougher on STRs, selling might not be a bad move either—just crunch the numbers first.

i provide dishwasher if we are putting a new kitchen. also a garbage disposal.sometimes i provide washers/dryers if i have extra laying around (i always seem to have them).sometimes i have purchased fridges and ovens since it's best to invest in capital expense and get a tenant than to have a house sit empty forever.our lease also states that tenants should purchase the appliance plan, which noone really does purchase. 

It seems that investing in improvements while I still live in the home wouldn't be tax deductible.

I was recommended to check out Maverick Investor Group and it certainly seems appealing that they find the deals for you as well as offer many guarantees on the rehabs and such.

Then there is city approval and whether they want a 2 to be a 4 (seems like the nearby properties might support it).

Please come down and see me and let talk about real estate.My plan now is looking for buy and hold and flips.If your 100% motivated for REI just like i am, come down and meet me.

Quote from @Bruce Woodruff: Quote from @Max Ferguson:Considering buying a property with (what seems to be) a well put together yet unpermitted ADU.

I found this fact sheet which seems to indicate it would be possible to evict the rent stabilised tenants so long as they haven't been living there for more than 15 years or are older than 62 or disabled: https://hcr.ny.gov/system/files/documents/2020/10/fact-sheet... 

Everything seems to work as is for the time being, but I'm budgeting for the roof and furnace replacement in the near future. 

.: Quote from @Tim Delaney: That seems odd to me assuming you aren’t in a highly negative cash flow situation.