So, for example, I find a ridiculous and killer deal. 

Then buyers will be looking at your postings first.My personal record for a killer deal for me AND the investor22 hours from me signing the option ( buy) paperwork to signing the assignment$50 ( fifty)… five…oh… FITTY dollars out of pocketMy “ option to buy price”..$15,000My “ Assignment fee” …$. $17,000Assignment deal completed 22 hours after I signed the initial docs.Sound like a rip off?

Normally, negative cashflow is a deal killer, but it sounds like your top criteria is appreciation long-term.

I certainly prefer not to do it that way, but it's not a deal killer IMO.

Unless you are getting this property at a killer deal, I would walk.

I do Coliving in the upstairs unit which is bigger and make killer cash flow!

My wife has a killer TC and based on what I know I she does very very well financially without ever leaving her home computer.. 

You don't care about cosmetic defects -- you want to know about the big ticket budget-killer items. 

But if your goal is to cash-flow out of the gate and your market can't support that strategy (unless you find a killer deal), then you may consider a pivot. 

That next door trailer may be a deal killer for you, or it might not.Given it is your first effort in a new town, I'd either hire an appraiser to make you more comfortable with your valuation, or just keep looking for a house that gives you more confidence.