Or you can take a hard money loan if you expect to get a job within a few months (the more expensive and risky option but possibly worth it if the deal is excellent and you can't get conventional finance)

Their high interest charges don't like cash flow, and in 5 - 8 years, you are now looking to do what you should have done in the beginning...get a 30 year loan. 

I should be able to increase rents to around $11k per month even with charging utilities on top as I update leases/get new tenants.You're correct on the property management, forgot to include. 

I found a property management company that charges 10% all in, no other fees, etc.Now, for only one property, do you recommend I landlord or hire it out?

;Starting over, and not being considered for a conventional loan as a new 1099 earner; Will not get to travel for work anymore; Stable work environment with people that I enjoy working withThanks for taking the time to read/answer my 234235290 word essay :)

I should also mention that I paid $1,000 towards my buyers attorneys fees and in addition he charged my buyer $850 for a grand total of $1850 in closing fees...so I am pissed off  that he took advantage.

Are there any conventional/local lenders who would be willing to grow with us?

The better operators will be able to charge more. 

This would either be living in a home that you can rehab as you live there (preferably for 2 years for the home gain exclusion so you never have to pay tax on the gain up to $250k or $500k if filing joint taxes) OR buying a multi-unit property and living in one of the units and renting the other ones (you can get conventional residential financing up to 4 units). 

On 7/16/2018 officers visited the home to serve outstanding warrants on drug trafficking charges on the tenant which turned into officers getting a search warrant of the property.