Rent or sell current primary residence

[Benjamin Thompson]

Looking for help analyzing my current primary residence to decide whether I should rent it out as my first long term rental or sell it. Although i'm completely dreading it, it looks like my best move to get started in REI is house hacking. Here are the numbers, let me know what you would do....

Condo - 3/2.5, 1950 sqft, good neighborhood, best school in the county etc....

HOA fees: $145 a month... covers trash, snow, lawn, insurance and all exterior maintenance.

Sewer-$30

PITI-$700

value- $122,500

balance-$101,000

Rent value-$1,250

The only money I have had to put into the place in 8 years is $700 for a hot water heater.

I'm just not sure if the cashflow would be worth having to deal with the HOA even though I like the idea of not having to worry about ext maint. snow, lawn etc.... With agent commission I would only be looking to get 12-15,000 out of the sale and I would be looking at a tri or fourplex FHA to replace it, spending the least possible amount of time in that (1 year) and then moving on from there. I was thinking about either a triplex or 4 plex as from what I understand as long as the other units rents cover PITI of the entire building then 75% can be used towards DTI ratio.

I'm sure I forgot some important info here, but what would you do in my situation?