Some thoughts to consider:If you sell now, you are unlikely to pay capital gains taxes as your first 250k (500k if married and filling jointly) aren't reported.Doing your first rental remotely is undesirable without 1.)

He is married with joint income of about 148k.

You could file "married filing separately."

In Florida where I live that amount is the first $50,000 for a married couple are exempt.So to put all that into action, let's say the previous owner paid $100,000 for the property 20 years ago and lived in the property.  

In Missouri, a married couple jointly owning LLCs is generally required to file partnership returns for each LLC, necessitating Form 1065 at the federal level and Form MO-1065 for the state.However, the IRS offers a Qualified Joint Venture (QJV) election for married couples, allowing them to avoid partnership classification by treating the business as a joint sole proprietorship.

I’m a 28 year old married man with a 3 week old son.

The best way to learn about how to really invest in real estate is to read books, listen to good podcasts, and pair that with going to in-person meetups so you can see people just like you, married with 3 kids, who are making it work for them.

All the friends I trust were out of town or married, and I was done living with strangers. 

I’d rather not do a single family again until my third house - I’m getting married in January and would like to be able to rent it without house hacking :).

Time spent as an investor or in activities not customarily done by an owner does not count towards the 500 hours.One thing to note is that if you are married, you can combine hours with your spouse's to meet this threshold.