Just as an aside, both plan to keep their owned real estate and lease it to the business buyer.I like that because it makes the business much easier to sell.

(Michael's posts are a great resource for this, but still no substitute for working directly with a tax accountant that's well-versed in all the ins-and-outs of this.) 

You have a good support system here, hopefully your brokerage does as well.

I am well versed in pretty much every facet of Real Estate: house hack, LTR/MTR/STR, multifamily, and fix and flips primarily.Aside from that I am also (somewhat) a serial entrepreneur, having started and sold multiple business' over the last 15 years.I also meet with 20+ professionals every week, through referral groups, meetups, and just 1 on 1 sessions trying to get to know people and make connections.I would love to chat with you if you are looking to meet people and get more information about real estate in San Diego!

(Doing this one well should help you with the following two.)The second would be to invest in your education on how real estate investing works.

If you cannot google and find a lender then there is most likely a reason why you cannot find a lender to do the loan.Finding a lender today is like finding a mcdonalds, they are all over the place.

-Management is low - you'll need at least 10% plus leasing costs - typically a month's rent for each lease-up, and sometimes a renewal fee as well-Insurance seems low-Are taxes accurate? 

Personally, I invest in properties in C-Class neighborhoods in my market (East Linden and Southern Hilltop), and they’ve been cash-flowing well so far.

You don't have to spend a fortune and buy a house directly on the beach to do well, but your starting price point for a viable option in this market is around $350-$450k for a solid 2-3 bedroom oceanfront condo or around $500k for a 3-4 bedroom house within walking distance of the beach. 

I really appreciate the well-rounded perspective you shared.