It depends many factors, such as your seniority and pay in your IT job versus where you would have to start in real estate.  

However higher property taxes when combined with a possible loss of homestead exemption will increase your monthly carrying costs on the property.If your plan is to return in 5 years then you may want to run some calculations on the carrying cost of the property versus what you think a similar (or same) property might be worth in 5 years.

You also want to look at their budget versus actual (income statement), delinquencies, minutes, reserve study (are they saving for future projects?).

Interview about three, You'll find that they're are some that will definitely want the long-term steady business versus the ups and down of vacation rentals.

I know a lot of investors lien towards leases with the option to buy agreements because you dont have to foreclose Versus a purchase money mortgage where the buyer acquires title. 

We’re looking farther North for a more suburby feel and to avoid paying a hipster premium.I’m now weighing cap rate versus quality of life.

The cost to keep them clean and functional is minuscule compared to the potential cost of repairs related to poor drainage (damaged foundation, water seepage, mold) all which occur over time and are hard to spot until it's too late.As a landlord, you'll always want to look the long term value of your property versus what is easiest and cheapest right now.

You can see first-hand how things run and even change a few things for the better; better to have solid home owners versus tenants as tenants do not treat the property with the same respect and care as home owners; look for a condo complex with a solid reserve; and lastly, if you are going to invest in a condo: READ the CC&Rs (The rules of the HOA community are set forth in what is called the Declaration of Covenants, Conditions, and Restrictions), very carefully.

Also, I weighed the benefit of getting into the particular property that I'm under contract on versus the short term opportunity cost risk and deemed it to be sufficient to take the funds out of the 401K.

You would have to calculate the savings from a quarter point off versus the buy down fee upfront and how long it would take you to break even to see if it was worth it or not.With higher interest rates in the future having the loan have an assumption option is important as well down the road when you sell.