You should know the area on a house by house level ideally, and you won’t get that kind of market knowledge by visiting a few times.

@Russell Brazil is right (and that's about when I bought my first house at 18% :-)The numbers will always work - or never work, it just depends on which property you choose to purchase and where it is.

Selling at $278,999Should I keep the house on the market ( delay my move )  and keep it as my primary residence while I save to buy a multi-family? 

I haven't done this as this is going to be my very first property, please feel free to ask any questions:Potential Rental Income: $1000/- month (Right now through housing, but rent is due for increase)Taxes: $2600/-Utilities Water/Sewer: $800/- (Rest of the utilities are paid by tenant)Purchase Price: $124,900/-

Plenty of parking above the house on a gravel lot4.

As far as the house, I would get someone to complete the outside and I would finish the inside and do all of the electrical, plumbing, trim, etc. and contract out the drywall myself.

If I go with the 5900 policy I will be operating at a loss and I will be forced to sell the house. 

I currently own a duplex in Massachusetts that I house hacked for 2 years (without even knowing that's what I was doing).

If one or two in 1000 houses would be open to a "cash offer" in the next 12 months, that means you have to market to them and the other 998 consistently for 12 months.

You are south of 70% LTARV, you're in an active market and in a good school district and you are not the most expensive house in the area.