It is not impossible but harder for sure.It comes down to the economic fundamentals and if the deal is good enough to take the risk.  

This is not impossible at all. done every single day.

He's long since moved from Seattle to Eastern Washington where living is more affordable, but the rising prices have crested the mountains and it's now just about impossible to find something nice-ish to rent within his budget. 

Priced out of CA investing and looking to go out of state I have been to KC and really like the city but its virtually impossible to get around the whole city and see all areas.

@Gehmelle Johnson   It's possible to do what you are asking but I can't imagine starting out of state without a SUPER GREAT absolutely perfect contractor.How to do this without being here to check on the contractor to start seems impossible to me. 

Until someone can understand what you want and need, it's impossible to advise you how to achieve it.

As far as "how long", that's impossible to say without real numbers.

You can get 30 year fixed rate mortgages whereas that's nearly impossible with commercial financing. 2-4 units you can also house hack which is a great strategy for someone to have their housing expenses covered.

I might even say it's impossible, since most of the areas in Winter Garden are strictly controlled by the township or HOAs.

Credit score is a very big factor in determining interest rate, so it's impossible to say without knowing credit score, along with the loan type.