I'm wholesaling in NJ and I have a bunch of leads where sellers would prefer selling with a realtor or their property is renovated and they want market value.

If you have little or no experience with property management I would recommend a single family house or a 1-4 unit to start with based on personal preference to get some experience before diving into the larger properties but nothing says you can’t buy a bigger one to start with if you feel comfortable with it.

Comes down to risk tolerance and personal preference.

I prefer higher priced properties for my IRA and that means a lot of down payment.

Is there a place that i can setup estimated value in search preferences (filters) ?

I did look up Airbnb in East Oakland, and surprisingly there are some properties that are doing very well, even in the hood, so I was toying with the idea. 

Currently self-managed, but prefer not to do this long term.

Does anyone prefer Airbnb over Vrbo or vice versa?

I would be inclined to order a deck cleaner/wash, a deck paint of your color preference, and general paint/staining supplies (brushes, rollers) from a nearby Home Depot/Lowe's, pay for them, and have them available for pick-up by the tenant at the contractor's desk. 

I've been following commercial real estate for the past few years and I've developed a personal preference for the STNL space.