These will be markets where housing is affordable for both residents and owners.

Instead of following trends, tailor your space to the lifestyle of your target market.

If I'm ever in need of a broker in the DE markets, I will reach out. 

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Yesir still operating in the MKE market. 

Purchase price: $35,000 Cash invested: $38,000 Another flip ready in the market. https://www.zillow.com/homedetails/4467-Sims-St-Columbus-GA-31907/76572533_zpid/

Record-breaking high prices in the upper end of the market skewing the entire market upward?

If you go the rehab route, you can refinance when finished with the work into a DSCR loan to get all/most of you initial investment back if you found a good deal.

I haven’t completely dismissed the possibility I can get into some great markets out of state, it’s just the unknown is so great about it, I haven’t given it a ton of thought. 

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.