These cities are the well known, sub 100k markets in the US.

However, purchasing the replacement property from an estate where your mother-in-law is the executor and other heirs are your wife's aunts and cousins raises potential related-party concerns under Section 1031(f).The IRS generally prohibits 1031 exchanges between related parties unless both the buyer and seller hold their respective properties for at least two years after the exchange.To stay compliant and avoid disqualification, ensure:The estate sells the property directly before any distributions to heirs.You hold the replacement property for at least two years.The transaction is conducted at fair market value with no prearranged agreements.Given the IRS scrutiny of related-party 1031 exchanges, consult a qualified CPA or 1031 exchange accommodator to structure the deal properly and avoid potential capital gains tax liabilities.This post does not create a CPA-Client relationship.

Do you have experience and know the cycles of your market so you know the best price?

Pushing into other, close-by, markets is the best (and maybe only) way to make it work.

You picked a great community to join.. have you checked out local comps to gauge the market vibe yet?

Not that I am aware of, but I am not aware of all softwares on the market. 

I used a hard money loan to purchase this off market deal.I rehabbed the upper two units within two and a half weeks and have a renter already lined up for one unit.

There are very few markets that cashflow with 100% leverage.

I am slowly going crazy with how expensive Massachusetts is and I am leaning towards looking at cheaper foreclosure properties.I understand there is some risk to this but I am beginning to think this is the only option I will have because of how fast the market is growing.Thank you for any insight you may have!

Is there anyone in your local market you could take out to lunch who does flips?