Thinking Outloud...Need more eyes!

[Louis Fabrizi]

Hi all!

Writing from the Northern Virginia/Loudoun County region this morning. Simply needed a place to 'brain blast' and get some feedback on a potential investment strategy for my family and I. For context, I work full-time as a Project Manager and just started a side-career as a real estate agent. Have already done a few deals and am optimistic about the next several years! Median home price up here is $550k, for reference. 

INVESTMENT PLAN:

- This Fall 2021, we will have fulfilled our Primary Residence occupancy requirement of 12 months after refinancing our townhome in Ashburn, VA. 4bd, 4bth. Would like to convert this into a rental for a long-term hold and sell it in about 15 years when my oldest son goes to college (or whatever he decides to do!)

- So, this Fall 2021 we'd like to buy another townhome in Ashburn, VA, convert former townhome to rental, live in new town home for a year, and then convert second townhome to rental. (Fall 2022) Same strategy of long term hold and sell in about 17 years (for our newborn son).

- At this point, we would then find a single family home a bit further outside of town to settle down in. (Spring 2023).

Questions:

- As long as I don't have two FHA loans active at same time (which I currently don't), are there any stipulations about getting multiple FHA's within a short (2 or 3 year) window of time?

- typically, how long before a lender will use 100% of rental income as opposed to 75% when talking about DTI?

- we have no other debt, so a few hundred dollars of debt here and there from a lender using 75% instead of 100% isn't a huge issue when it comes to purchasing more properties.

- does anybody foresee any challenges with this strategy?

*NOTE: When we get to the point of purchasing our 'settle-down' home, I'll have two years of real estate income to add to my day job. Hoping that'll help increase our buying power when factoring in any potential debt we would then have since a lender would be using 75% instead of 100% of rental income to offset DTI.

Numbers below are pretty darn close to what the rental deal(s) will look like:

Monthly PITI (includes HOA): $2,100

Rent: $2,500/month

Thanks in advance for your insight! I trust this community greatly and really value your thoughts!