What makes you think starting in Section 8 is a good idea?

Multifamily properties can be a great way to build wealth, but only if they align with your risk tolerance and lifestyle.Hearing from others who’ve been in similar situations might also provide reassurance and ideas.

Well, others won't want to either.You get the idea.

Any idea of lead times? 

Would love to connect with local RE agents and have an idea of the market situation in SA.

We like the short-term rental idea because we could stay at the property ourselves when we want - summer break, spring/winter breaks, etc.Our budget will be right around $1M or less ideally, and we would like a short distance to the ocean.How likely is it that we could find a property as described above and have it cover or come close to covering the mortgage? 

Here is a good five minute bit from all in podcast discussing this topic https://www.tiktok.com/t/ZP8F5dV3K/

Again, the BiggerPockets store has some books on this topic, or you can learn about it by watching podcasts, reading blogs, and interacting on the forum.

Also what does the city say is the assessed value of the property on your taxes (it will be different than the appraised value, but should give you an idea).

That is definitely a good idea and strategy!