First Home Orlando - First Hack

[Evan Linder]

Hello,

I have delayed gratification for a number of years in preparation to buy my first home in the Central Orlando, FL area.  My short term goal would be to find a house hack property that would set me up with a long term goal to repeat the process many times over.  I know there's a learning curve to this and I'm not averse to making some mistakes.  However, I am here to seek advice in avoiding the biggest ones.  

A few scenarios I'm pondering below... 

1) Rent rooms:  Easiest and quickest option but also my least favorite since the whole privacy factor.  What layout works best for those currently doing this?  What type of lease term agreements have worked best with your roommates? 

2) Multi-family:  I have not seen a decent side by side 2/2 multifamily for sale in any decent areas in the past 6 months for under ~$600k.  Beginning to think this won't be realistic my first run.  Any of the ones I do find are over an hour (without traffic) outside central Orlando where I'm based.  Let me know if I'm missing an angle on this. 

3) Single family and add ADU: Let's say I get a 3/3 or 3/2. How much should I expect in renovation cost and permit red tape to convert a section into an ADU. What characteristics would make this the easiest to do? Big garage? Sun porch? Detached garage? Large yard? For those that have done this, what floor plans make this make this as painless as possible for a novice?

4) Loans: I'm in great standing for all standards when qualifying for a loan. I qualify for a conventional with putting some money down. Since I qualify for a conventional, should I be going that route as opposed to a FHA? How negotiable are interest rates with a mortgage broker? Again, with the long term goal in mind, what's the best option for repeating the process every 1-2 years when considering loan options.

5) Agent: I have not tried the agent finder yet and wanted to ask on here first.  Any agent can find me a 3/3, I'm looking for someone that understands what the long term vision is and how to get it started for long term success.  

As they always say on the podcast, the key is asking how can I do this?  What other big questions should I be asking?  Thank you