Although in the last couple deals most have come out as 506C deals where only accredited investors are allowed, there are still 506B syndications where you can be a sophisticated investor (self proclaimed) so you don't have to be accredited.

The loan is with you, not with your tenant, so none of that means anything to them - in fact because you live in one unit and it's under 4, if you were self-managing you don't even have to abide by fair housing laws (at least on the federal level). 

I would like to start close to home as I plan to self manage the rental side of it.

Remember, the notion of amassing wealth without investing is a dangerous myth perpetuated by self-proclaimed experts.

It’s worth considering self managing as a STR for depreciation benefits if the demand is there 

I am not a PM, but I do self manage about 50 units.

One thing to be aware of is the FHA multifamily self-sufficiency calculation which determines if a property can generate enough rental income to cover its mortgage payments.

Charming, smaller coastal towns with a slower pace of life, natural amenities, seclusion and semi-self sustainability are high on the wish list of many high level clients and investors. 

As far as self managing, it’s fairly easy.

Remember, the notion of amassing wealth without investing is a dangerous myth perpetuated by self-proclaimed experts.