You can talk to a private investor, but not sure I see a big enough profit in your deal to take it on.Start living like no one else does, get a second job or a better job, so you can save $20-30K and you can make this happen.I've had to pass on two deals 'cause I didn't have the cash to put 'my skin in the game' (just put $70k into buying a primary residence).

With wholesaling, you're looking at the after repair value and the ROI for the investor buyer.In the simplest of examples, say that $100k property would be worth $200k after $40k in repairs, you put it under contract for $80k (the seller gets $10k profit) and assign the contract for $15k, that leaves a good profit margin for the investor buyer.

I can absolutely say that investing there has been VERY profitable.

You need to lay out who owns what, who pays for what, who is responsible for what, what profit your each entitled too and many many more things.

But isnt that more of a speculation/gamble as opposed to tangible money?

This is circumstantial however, if you’re in a community property state, because you’re married she will have to qualify with your debts factored in as well (again this only applies in community property states).So all your liabilities, net profit on your current FHA property,etc.

It's a little bit of a gamble, but if it's a relatively small volume then you have more possibilities.Is there anything stupid about this strategy?

Starting late literally doesn't exist.Learn and research other profitable markets!

I have to make sure that a property will rent for more than I pay for it to make a profit. 

I seem to have 1-2 people a week now reaching out to ask for PM advice in Milwaukee and thinking we need an additional market due to 1) pricing and 2) diversification.Fort Wayne IN still works for us but is getting pricy and with lower rents maintenance and eat into profits - Would like to start converting this properties to seller financed deals over the next few years.