You get that freedom to make the choice versus being restricted by bills, cash flow, net worth, etc.Each level of net worth is not all sunshine and rainbows.

It seems like nothing cash flows unless I do a STR, and decorating an Airbnb alone eats up a large chunk of my cash.

Break out single family/condo; then 2 units then 3-4 units all have different rules. 1-2 units is far easier to get approved verses 3-4 which have extra conditions to ensure that the whole project cash flows with market rents minus the one owner occupied unit. 3-4 units you need much larger down payment - as in no 3.5% downSecond home programs are for one unit types: SFR/condo/townhouse.Owner occupied means you live there and your insurance policy matches.

I have yet to analyze it from a cash flow perspective. http://mattiasclymer.funkhousergroup.com/listing/5... 

Also make sure to keep the area clean so that trash doesn't pile up in there. 

And unfortunately, with the low margins in SFRs in basically all markets, once you add in $1k-2k per year of travel cost, you are likely to be cash flow negative anyways.As for me personally, it may be the level of control that I seek or lack of trust that anyone knows what I want as much as I do, but I would never buy a house sight unseen.  

Subsequently, we facilitated a connection with a buyer who leveraged the cash flow until the owner-occupant market yielded a positive return on investments.

But if I can't sell quickly, I could rent them and have multiple cash flow (because of the different income sources of the different tenants in the same unit) and wait for the market to recover and then sell the unit.Please let me know your comments and suggestions about this information.Thank you everyone!!

If you think about it the tenant is the real cash flowing asset.

Are you cash flowing the property?