Most in your shoes want to move as quickly as possible and sometimes slowing down & being more deliberate will save you time and money in the long run.

I would prefer to self manage to avoid the high poperty management fees (I think its around 10% + 1 month leasing fee, etc.) and I also worry that the property manager will likely not be as dilligent in finding high quality affordable vendors, etc.I see 4 major pieces of work1) Tenant finding: I feel comfortable doing this remotely.

If I were in your shoes, I would change my mentality to how can I convince an appraiser to give me more value to what is the worst case scenario, if the value comes in lower. 

Consider your comfort level with managing several mortgages and the risk of vacancies vs a slower but potentially more rewarding path to ownership.

Even if you're not making much profit at the start because you're investing in a better area, it should work out fine.If you're losing $100-200 per month but have a stable job, you should be okay.Most people get rich with real estate through property value appreciation rather than cashflow.If you're comfortable living with roommates, you can purchase a house in a good area you like and rent out spare rooms.

My issue is that I come from a low income background and have fought my *** off, pardon my language to get to where I am now and comfortable.

Perhaps this would make the lender more comfortable while giving you the benefit of settling with a shovel ready lot. 

I would prefer to self manage to avoid the high poperty management fees (I think its around 10% + 1 month leasing fee, etc.) and I also worry that the property manager will likely not be as dilligent in finding high quality affordable vendors, etc.I see 4 major pieces of work1) Tenant finding: I feel comfortable doing this remotely.

Travel is mine, I wanna see the world, meet people, and experience life outside my comfort zone. 

If you don't mind providing some data for me to reference I'd appreciate it, but understand if you want to keep some or all personal--namely I'd be interested in approximate location, bd/ba count of your property and the rent % increase (or if you're comfortable sharing actual prices) implemented between your last tenant and current one.