If you want to experience landlord issues, you can fha a duplex or buy an sfh as an investment property & that $250k will easily be spent. 

My main issue is employment history.

My realtor did a comp search and says the home is worth about 730 with the comps in the area, I spoke to a bank in regards to Cash out refinance and I can pull out 80k (which I will use to buy another property) my mortage will be 3k per month...my only issue is that my interest rate is 3.75 on my current mortage and will be 4.6 on the refinance but will be getting rid of the fha loan.

Now the land is not worth nearly as much as the collateral the bank issued their loan on.  

I always run my STRs with LTR rents also, as my back up plan if cities change permits or cause me to switch to LTR 

Maybe you could get some information when various states and utilities issue RFPs for new generation. 

Someone I know owns section 8 properties, he doesn’t have any issues and the rent gets deposited directly to his account.

Not going to spend a lot of time defending the location I invest in, because I feel like the proof is in the numbers....my "issues" and "bad tenants" are very far and few between.

Just pulling something from the internet (don't trust everything you see so take this with a grain of salt I'm not a lawyer): "If the building in question isn't officially designated as an SRO or hotel, it is illegal for landlords to rent individual rooms to tenants for a number of reasons, including that it could allow landlords to evade the maximum rent permitted by the Rent Stabilization Law and Code."

It can hurt your sellers ability to buy another home because of DTI issues.4.