This implies if you sold and bought the exact same house your current property tax would increase substantially.  

It also did not have a pool like your property so that would probably lower the desirability as well.

Quote from @Devin James: Gross Margin is an important calculation for developers/builders.Gross Margin = Gross Profit / RevenueWe shoot for a 20% gross margin on our New Construction HomesReal #’s:Home Sales Price: $374KClosing Cost: $18,700Cost of Construction: $258KLand Cost: $30KGross Profit = $67K$67K/$374K = 17.9% Gross MarginCame slightly short of our goal of 20%Homes Values and Build Costs are constantly fluctuatingI wish we had a crystal ball build larger homes. average new build in our market is 2200 square feet, 4 beds, 3 baths, 2 car garage and sells for 515k. construction costs lower if design is good and find the median or average home sale price and push that up. my guess is you built too small. 347k is cheap. we target 429-479k price range in columbus ohio for single family homes and also only purchase close to urban core where premiums are 20% higher and we build smaller like 1500 sq ft where price per square foot goes up. 

Regarding price, do you have any suggestions on how I can get him to agree to a lower price?

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Getting a loan to payoff another loan with a lower interest rate doesn't make any sense. we do private lending and can get double digits returns consistently.

Is an IRA subject to capital gains tax?

I would not offer furnished rentals in lower income areas. 

If I can park the 388k ($415-27k) for one year at CD rate of 4.5% and then est 300k (after paying cap gain/depr recap) at 3.0% (assume CD rates lower) that interest income of about 24 months net of ordinary income tax is about the same as my current mortgage.Trying to play devil's advocate and think why selling this year does not make sense. 

For investors, the current market presents a mixed bag: while short-term rental income may be lower, Miami remains a strong market for long-term growth as affordability attracts more tenants.What’s your take on Miami’s rental market?