@Joseph Scaglione CT is not a tenant friendly state relative to other southern tenant friendly states.

Concerning your advice on the 4-plex, I am in Southern California and most multi families seems to go for 800K to 1.2M so it would take a significant amount of time to build up even the down payment.

We are in Southern California.

I'm leaving my hometown of Southern OR towards the end of 2021.

I'm originally from Southern California, so i'm very excited to be able to go somewhere with affordable homes!

What ever it is it will be shorter than a similar property in a south eastern state.From looking at the generic website that come up when you look up “AirBnB” statistics it seems that the hot season is 4.5 months out of the summer.It certainly does not compare to the southern states equivalent imo.it does have the potential (like some of the other comments) to have a winter potential but according to the (generic) websites mentioned above the average income for a 2BED/1BATH is ~300$ for the month :( 

Here in Southern Delaware all the first floor walls can be put up in one day.

Where exactly, looks like maybe between Lake Worth road and Southern, near Dixie?

I am a potential first time investor based out of Southern California. 

Your best bet with that kind of budget is sticking to the outskirts of the MSA and the Southern counties.