Madison is also a great city to invest if you're looking to gain equity a bit quicker than other parts of the state.

Originally posted by @Cara Lonsdale:Having access to the MLS and your lockbox key will allow you to search for properties in real time and gain access/entry when you want to view. 

I agree with most people in this forum that mid-term rentals are on the rise and gaining popularity. 

Lowering it by $100 could gain more interest & lease it out sooner.

I am just unsure if we can avoid capital gains taxes if we do the seller financing route. 

Look If you are thinking of house hacking, then who cares if the market is overrated or not, as of right now if you have been renting all of these years you have been loosing $25-40k each year by renting and not gaining from the Miami appreciation of the market.

@Rachel Seymour-NewtonIf the smaller property is a strong deal with solid cash flow and tenant demand, it could make sense to buy now and start gaining experience.

Most come out ahead over an extended period of time by buying better quality assets where they perhaps have to leave some capital in the property but find themselves able to sell for real gains or refinance out appreciated equity and scale more effectively that way. 

If you do a 1031 exchange, you can defer both the capital gains tax and the depreciation recapture, which is a nice benefit.

Because I benefit from more business oriented books I also like Who Not How and Gap and the Gain by Dan Sullivan and Ben Hardy.