Since it sounds like you have strong W2 income and would probably be okay paying the mortgage sometimes, I'd even explore a 5-10% down payment option.

Buying a single-family home with a detached garage and converting it to an ADU is much simpler.

Focus on areas with strong rental demand, like Broad Ripple, Fountain Square, or near universities like Butler and IUPUI.Maintenance Costs: Indiana weather can be tough on properties, so budget for seasonal maintenance like snow removal and HVAC servicing.Additional AdviceKeep an Emergency Fund: Unexpected repairs or vacancies can arise, so having 3-6 months of expenses saved will help you weather any surprises.Build a Reliable Team: I have lists of contractors, handymen, cleaners and property managers if you'd like me to send.Good luck with your property and future expansion!

I’m open to either a townhouse or a single-family home, but I’m definitely trying to steer clear of any crazy HOAs that eat into cash flow (you know what I’m talking about!).

There are many here in my local area and your area is likely to have the same type of meetings.Most of the deals that I fund are by meeting investors in person at these groups and creating strong relationships. 

., "I will buy at least one single-family home, duplex, triplex, or fourplex before the end of 2019") and then do it.

If you are looking at FHA because of credit score, then I would work on credit scores to qualify for conventional financing or see if you can get a very strong coborrower with high scores.  

Your strong foundation in the stock market and tech background positions you well for success in real estate investing.

Managing from afar can be done on single family homes with a few properties, but you'll still need a solid leasing agent and handyman which can sometimes be hard to find. 

Building strong relationships with lenders is critical and the easiest way to do that is to be easy to work with.