Investing to purchase a forever home

[Brittany Bauhaus]

Hi all, I'm new to the BiggerPockets community. 

I've been researching real estate investing for a little while now, and I feel ready to take the plunge. I'd like to explain my particular situation: I'm not here to make big money. I'm fairly certain that makes me an outlier in this community, but please hear me out: I currently live in Santa Barbara, CA. Everything is way too expensive here and it's not my favorite town, but I have to live (and rent) here for the next 8 years. My end goal is to buy a home in Ventura, CA (my favorite place on earth) with an ADU on the property. I currently can't afford to purchase such a property, so I need to work up to that point. My girlfriend has land in Costa Rica, so we'll eventually split our time between Ventura and CR. I'd like to rent out the ADU consistently, and also the main house when we're out of the country. Of course, eventually it'd be nice to live off some passive income via real estate investments, but I actually love my job and am not concerned with needing to quit or put all my eggs into the RE investment basket right now. But my definite short(ish) term goal is to buy this home within 8 years. Now, my respective investment scenarios:

1. I can purchase a roughly $300k condo in Ventura or Oxnard as an investment property and rent out the condo for a fairly small ROI. Keep in mind, my main goal isn't to purchase numerous properties right now. The plan would be to sell this condo in 3 years, buy a new one, rent it out for a higher rate, sell in 5 years, buy a forever home w/ADU.

2. I can purchase 2 homes in Ohio or Alabama for roughly $100k each, rent each of those out for a small ROI, sell in 3 years, buy a multi-unit property, sell in 5 years, buy a forever home w/ADU.

*Number 1 seems more appealing to me, as I'll be the private landlord (and can save on costs there), and I know those cities so I feel comfortable choosing the right property.

*Number 2 seems like it will possibly bring in more cashflow (once all the numbers have been sufficiently crunched), but again making huge amounts of cash isn't my immediate goal. I also don't feel as comfortable purchasing a property I've never seen, even though it's turnkey. I'm researching turnkey properties all over the US via realwealthnetwork.com and am now focusing on Ohio and Alabama.

I want to make sure I'm building up the most equity in the shortest amount of time. I have $40k-$60k ready to invest. I want to make sure I've covered all my bases and choose the path that's the surer route to reaching my goal.

Any/all advice is welcome, and thank you for your time!

bb