Or am I barking up the wrong tree?

@Zac KucharekI house hacked two properties (SFH's) from the 1970's and in roughly 4 years owning 2 properties I've had to: - Replace a roof - Replace both water heaters (1 water heater leaked 6 months after replacing it which was a $2,500 fix to mitigate minor flooding) - Remove a pergola that was damaged from the roof replacement- Remove a tree - Replace a furnace - Replace multiple ceiling fans - Replace interior shower plumbing in upstairs bathroom - Replace the main water line-  Pay for many pest fixes - Irrigation/drip line replacements - Replace a microwave - Redo electrical in the garage - Fix a newer furnace multiple times - Fix washer/dryer in both homes multiple times I'm not saying this to scare you by any means, as these two homes have completely changed my life for the better. 

I've been counting the days in anticipation of this event and I'm ready to start looking at a second property, or so I thought before talking to my broker..Originally, the plan was to finance tree first duplex with an FHA loan, live in one side for a year and then look for another duplex afterwards, finance that with a similar loan, live there for one year, rinse and repeat, etc.I knew that I'd eventually have to find another way to finance these deals, but I didn't think it would be before buying my second property!

That's one reason I decided to post my question - it's easy to get focused on the trees and forget what forest is most desirable! 

If you close on the property and then discover the roof is leaking, the main sewer line is nothing but tree roots, really any major expense, that can easily put a borrower in a position where they do not have enough actual cash to solve the problem, so the property loses value due to deferred maintenance, or the borrower digs themselves into more debt, making it even harder to get another loan to cash me out of the equation at that  upper 20% of equity. 

I'd recommend reading this article by David Greene: https://www.biggerpockets.com/blog/core-four-real-estate-tea... 

Seems plausible enough, with ice-laden tree branches falling on power lines and such.

I got myself 10 acres in Joshua Tree at auction.

The city will force you to put in a 3x5' meter vault in the parkway (or under the sidewalk if you have a big parkway tree in the way).

Full rebuild and removal of 2 big trees.