Analysis on first investment and advice on second investment

[Adam Blandford]

I am a 24 year old Marine Veteran that separated active duty service in July 2021. I bought my first house in September 2021, a 3 bed 1.5 bath 1200 sq ft with a detached garage. Purchase price 355k on a 5% fha loan. I have been living with 1 roommate a good friend of mine and using the extra room as a office which was nice for getting adjusted to school. I have another person moving in a week from now. I will pay for some utilities but the mortgage + $150 is covered by their rent. 

Refinanced, the place could cash flow in the 1,000 a month range. Short term rental, the estimated max yearly revenue on the airbnb calculator is $56,289. The yearly cash flow from the STR could be nearly double the yearly cash flow from LTR.

My goal is to repeat the same model. Find a place that I can get on a 5% down fha, house hack for a year and repeat. The first investment, my father was the guarantor, as I did not have a stream of income. 

Does anyone have any recommendations or experience, specifically road blocks that will restrict me from closing the second deal. BTW I have looked into cash out refinance and could utilize that if I renovated the two bathrooms.