This lets your HSA grow, and since qualified withdrawals are tax-free, putting more aggressive investments in an HSA can pay off in the long run (similar to the “put your risk in Roth” idea).4.Rollovers & Debit CardsMost brokerage HSAs come with a debit card, so spending isn’t too hard if you ever need to.

No, we can do everything ourselves and not spend more money than we have to.

I spend a couple hours a day driving to and from work so I have plenty of time! 

Because for a certain type renter it’s just SO easy to continue renting fully furnished rather than having to spend $20-40k on furniture; come up with a down payment on a house purchase; and or worry about repairs and maintenance.  

I have a W2 and can survive off it, so I never really needed my RE profits to spend on myself.

You can probably spend much less time touring and learning new things than you would in an otherwise unfamiliar market: laws, neighborhoods, tax considerations, etc.Scenario 2: Stay in Place & Buy an Out-of-State Multi-Family Property1. 

If you are going to focus on listings only list ones that are priced well to sell before spending your money.

You will also quickly learn how to manage properties well instead of spending decades figuring it out like most investors.

before you spend another PMCs time. 

It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).