My point is I think the technology is going to be much better/affordable in even 5 years, so why lock into a system that is going to need to be replaced around time of payback?    

So unless you plan on getting a permit for those and paying the cost to install them, kiss this project and your numbers goodbye :-)And it's much more likely the fourth building is going to need to be torn down than it is likely to be easily converted to a fourth unit.

I'm likely going to need to finance with a FHA and a family member co-signer/borrower.I know this is a very difficult and very hot market and based on preliminary research a duplex likely won't cut it but triplex and 4-plexes may be unaffordable when it comes to even a 3.5% downpayment and PMI fees.

Well, you're probably going to need to raise a lot of private money to finance all of that.

@Morgan Madill - you're going to need your W2 income to qualify to buy for awhile.

Probably going to need to be a private money lender since most mortgage brokers and banks will not do a loan under $100k. 

See, a motivated seller, is not someone that “wants to”, “needs to”, or “has to sell” their house.

I have almost 30k available, but with some of my calculations using the BP Rental Calculator to get a good cash flow, most of these properties are looking to need about 60-70k down.Now, we own our SFR and bough it at 224, and now it's been assessed at about 275 according to our property taxes.

I had to get creative here, because even with 10% down, some closing costs and work I was going to need $300k, which I have nowhere near.

You could consider using a hard money lender to flip a property but $25k is still on the low end for what you're going to need to get into a small deal but its just at the bottom end of possibilities, finding the property to flip will be by far the hardest part.