Maybe find a home in the 150-250k range then after living in it a year and renovating, rent it out and refinance to use for a downpayment for a second single family and start down that path.

@Kirk R. no because that price point is so different than anything else, I was referring more to houses in the $75k and up range, which is going to be a pretty big majority. 

What area and price range?

For this type of investor, their time is valuable, and trying to manage a long range rehab may not be worthwhile.

The areas I have started looking range from like Framingham, Sharon, Franklin, Medfield, Westwood, Norton, Foxboro, etc. basically looking at all towns in a 25/30 minute radius from my wife’s work which is in Medfield.

Property worth about 1.4-1.5 range.  

(Theres a fantastic hospital less than a mile away so maybe travel nurse housing is an option here for more income) Market rents for the 2/2 house would be between 1900-2200For the ADU its be about 1500-1800Total rent range 3400-4000Property taxes are 500-550 a monthRough cash flow 1100-1250 (year one)The inside of the property would need to have: -All the flooring replaced. 

If I remember correctly, somewhere in the 6 percent range?

I haven’t been able to see any construction in the area, however, in the last 6 months homes are being sold in the $600k-$900k range.

This rehab is likely $100k based on what I am hearing and with an exit of $275k (you need to use the lower of the range in this case), then your max offer would have to be in the $110k range, I doubt the seller is willing to take that big of a loss and reduction in price but you never know until you ask.