Obviously if I intend to have a top performing STR in this market, my buy box will allow for a much higher max purchase price, but I wouldn't feel comfortable with shooting for the max if there aren't clear ways to beat these competing properties.

Alternatively, happy to be a resource should you need help identifying opportunities and analyzing deals. 

If a storm happens immediately after you replace the roof, the actual cash value is the same as replacement cost, so you've lost nothing.The only thing you would have to worry about are items you did not intend to repair

And using the process buy a new property or properties that you also intend to hold for investment use.The issue for you might be that you purchased this property with the primary intent of selling. 

Specifically:Licensed and Insured Contractors:Strong experience in fix-and-flip projects is preferred.Proven track record for meeting deadlines and staying within budget.Interested in building a long-term working relationship.Real Estate Agents:Knowledgeable about properties in Chattanooga and surrounding areas.Skilled in identifying high ROI opportunities for fix-and-flip projects.Open to partnering with an investor for repeat business.If you or someone you know is a great fit, please comment below or send me a direct message.

Since your wife will probably never want to learn as much as you do about real estate investing I would use it as an opportunity to really make sure you understand it by explaining it to her, if you can teach it to her you will gain a much deeper understanding for yourself.My question is though, if you want to be a real estate investor, why did you sell your only real estate investment to become a renter?

Sphere of influence purchase - off market opportunity.

One of those options is to let the tenant know you won't renew their lease, then offer them the opportunity to leave early if they find another rental.

We appreciate you giving us the opportunity to review your property.Best regards,"I replied back asking for more specifics, wondering if it is the Milwaukee market, the Wisconsin market, the multi-family market, or the property itself, and I got crickets....At the very least, I should get better customer service explaining why.

Philly was the land of unequal opportunity where certain blocks have more pollution, crime, problems.