It sounds like an ideal location for renting.

The property has become an ideal "piggy bank" for cash out from time to time to purchase additional properties.

Hey Gang - I'm looking to locate a lender who will help fund a condo flip in central Connecticut (ideally also fund reno costs).

Ideally, I would like to target an area like Hoboken/Weehawken/Jersey City to potentially live-in and/or house-hack with a multi-family as someone in my 20s. 

The fact is, he will have trouble saving up for 2 down payments within the next year, so if we invest in a property together, it would be ideal he live in the property for his sake.I've suggested that he should pay the full rent in the form of owner contributions (or some other way to not get double taxed on his dollars) to an LLC we would own (we're intending to buy a 6+ unit property) to make up for the loss of income by him occupying the unit.

Ideally I would like to brrrr but even the good flips will lose a lot of money on the rent side of it.

Property is a side by side duplex (each unit is 900sq ft, 2bdrm/ 1ba) One unit is vacant and I plan to use it as a LTR, while the other unit is occupied by a tenant who is paying way below market value at $645/month and I would ideally be getting around $1200/month.

The zones benefit first time home buyers, but as an investor the locations are not ideal.

I’m self employed, and had a co-signer on it - ideally, I want to refinance at some point in the next two years, get the co-signer off, hopefully get some cash out of it and do this again.

The best thing to consider when looking at a deal is having accurate information and numbers on the costs/expense, the loan/financing, and income (either actuals or proforma estimates).Run scenarios at the ideal conditions and the worst case.