Instead of evicting them, i was thinking is there some way that I could rent it back to him for very cheap (mainly to cover just the taxes/ insurance) ie 2k a year rather than the going rate of 2k a month for similar properties.

Taxes were $1363 a year.

I have over a hundred rental units I own and operate in Utah everything from homes and condos to larger multifamily.Salt Lake County has higher property taxes and is basically built out already and Ogden even though you can find good opportunities in the long run it won't be able to compete with South Utah County or Eagle Mountain. 

They are so tax beneficial! 

This is obviously much better than $1,400 per month.On top of that, you will now get 2x the depreciation write-off so your taxes should go down.On top of that, you will now get 2x the appreciation when real estate price go up.On top of that, your tenants are helping you pay down the loan, initially at about $100/mo for both properties, which gradually gets better and better.On top of that, you now have more units so if one or two goes vacant, you have more renters covering the losses of the vacant units.If you want to keep these properties, I would do a cash-out refi and go buy more rental real estate.

I know that i could buy my next multi family property as a primary residence close by move in, rent half live in the other and than rent where i am now which would cash flow upwards of 1k monthly, or i could buy another multi as strictly an investment property out of state which would be a lot cheaper (taxes and cost of property) and a lot more landlord friendly laws than New York, i guess i’m just undecided on which route i want to take and I’m trying to weigh the pros and cons of each scenario.

Then there’s this glorious tax season where you realize how many things you get to deduct that others can’t, while sheltering your income with depreciation, and earning tax free income with appreciation.

If your not ready to spend money on a software you can use tax records.

Lots of depreciation you will pay no tax maybe even shield some W2 income.B.  8k maybe 10k if you pick the right guy to lend your money to in interest income you will be paying much higher tax rate on this income FYI no depreciation expense. 

However , properties taxes are due like roughly 12k for the two lots.