The successful wholesalers are the ones that are direct with the seller and have done an analysis on the deal to show it can be a successful investment (always double check with your own)totally agree, I would add the don't act sketchy and present their available homes in a consistent/professional manner to buyers. 

The property, though is not beach front, nor does it has ocean view, is just a short drive from some of the best beaches in the west, which are great for surfing, snorkeling, SCUBA diving.In the 1.21 acres there is a main single family home (4 br) which was divided in two sections one of which is being rented.

I'm imagining something more like add a wall, turn a bedroom into a kitchen-living on one side and a formal dining room into a bedroom on the other side, maybe add a half bath in each unit.

I’m not looking for a step-by-step guide, but I know I’m not the only one in this position.

I am adding about 20 more this year, but there's one small pocket I'm struggling with the financing on (honestly, due to Huntington Bank dragging their feet on items, etc.), so I'm seeing what other options there may be. 

Any one investing in Windsor? 

A common pitfall is treating each deal as a standalone transaction instead of connecting acquisitions, financing, and project management as part of one cohesive process.

One of them is in TX, another one in MA and I am not sure about the remaining. 

So, Anca, your parents can 1031 from one property into more than one. 

Then again no one gets into commercial dreaming of being a handyman.