Only part of my strategy I'm unsure of is how to deal with an awesome tenant who treats your house like gold who simply cannot afford to go as high as the market will allow.

update outdated sink and bath fixtures (no gold fixtures), update cabinet handles. 

Your employer matches this amount.Since you're self employed, you get to pay both your portion and the employer's portion, which is where the 15.3% comes in.This is NOT your income tax bracket.Tax brackets are determined based on your marital status and overall income level as follows:2016 Federal Income Tax BracketsSingle filersMarried Filing Jointly or Qualifying Widow(er)Taxable incomeMarried Filing SeparatelyTaxable incomeHead of HouseholdTaxable incomeTax rate$0 to $13,25010%$13,250 to $50,400$1,325.00 plus 15% of the amount over $13,250$50,400 to $130,150$6,897.50 plus 25% of the amount over $50,400$130,150 to $210,800$26,835.00 plus 28% of the amount over $130,150$210,800 to $413,350$49,417.00 plus 33% of the amount over $210,800$413,350 to $441,000$116,258.50 plus 35% of the amount over $413,350$441,000 or more$125,936.00 plus 39.6% of the amount over $441,000Married Filing Jointly or Qualifying Widow(er)Married Filing SeparatelyTaxable incomeHead of HouseholdTaxable incomeTax rate$0 to $13,25010%$13,250 to $50,400$1,325.00 plus 15% of the amount over $13,250$50,400 to $130,150$6,897.50 plus 25% of the amount over $50,400$130,150 to $210,800$26,835.00 plus 28% of the amount over $130,150$210,800 to $413,350$49,417.00 plus 33% of the amount over $210,800$413,350 to $441,000$116,258.50 plus 35% of the amount over $413,350$441,000 or more$125,936.00 plus 39.6% of the amount over $441,000Married Filing SeparatelyTaxable incomeTax rate$0 to $9,27510%$9,275 to $37,650$927.50 plus 15% of the amount over $9,275$37,650 to $75,950$5,183.75 plus 25% of the amount over $37,650$75,950 to $115,725$14,758.75 plus 28% of the amount over $75,950$115,725 to $206,675$25,895.75 plus 33% of the amount over $115,725$206,675 to $233,475$55,909.25 plus 35% of the amount over $206,675$233,475 or more$65,289.25 plus 39.6% of the amount over $233,475Head of HouseholdTaxable incomeTax rate$0 to $13,25010%$13,250 to $50,400$1,325.00 plus 15% of the amount over $13,250$50,400 to $130,150$6,897.50 plus 25% of the amount over $50,400$130,150 to $210,800$26,835.00 plus 28% of the amount over $130,150$210,800 to $413,350$49,417.00 plus 33% of the amount over $210,800$413,350 to $441,000$116,258.50 plus 35% of the amount over $413,350$441,000 or more$125,936.00 plus 39.6% of the amount over $441,000

Update them weekly - so they know the status of your job and commit to showing up close to when you're ready.

"A bird in the hand is worth two in the bush" as they say.I think ideally it might make sense to have an assistant to call people to let them know of receipt, status and to turn paper around if that's all that needs to happen to maintain professional courtesy.

Most deals require accredited status which may be a hurdle.  

One of their guests brought it up while listing ways to follow up with them.

I plan to use a VA loan when I leave active duty service but since that isn't an option for you, find and listen to podcasts the guys do with guests who explain what they have done in the past.

These seem like a gold mind to me in terms of cash flow, but I see several of them in seemingly good condition languishing on the market for months when more traditional homes in the city are under contract within days.For example, here's one such house I'm looking at that is very common around here:Asking price: $52,000908 sq ft, 2 BR, 1 bathNo garage, small lot, siding/roof are <3 years old and mechanicals are <6 years old. 

For example either the house has been on the market for sale 15 days, and already in pending contract status (Hot Market).