Or is there a workaround, for example if they move out then move back in? 

I would recommend starting with fix and flips or BRRRRs then moving into ground up. 

Also, if the Land is owned in a Corp or LLC it may be a problem to cover it though your Homeowners. 

What happens if your friend moves away too, and you need to hire a manager?  

I think looking to get face-time with someone who is experienced in this specific situation and market status would be really helpful to answer some internal questions and provide guidance and external motivation to make a decision and get moving. 

Congrats on taking the first step, usually people get hung up on only one strategy, and the best way to start your real estate investing journey is house hacking with lower down payments and interest rate since it is a new primary residence, especially since you can probably rent out your primary and cash flow when you move out.I'm a local investor and realtor here in Denver metro, and I've found success with house hacking here in Denver for myself (rent by room, Airbnb, Section 8, LTRs, etc) along with my clients too.

I’ve moved into the Ohio market wholesaling and have had some marketing success with much cheaper spending.

Many of which are on a fixed income, and Dad is concerned about people moving in the winter when it's cold.

I’m trying to get the ball moving a little faster than what it is and with not being able to cash out or Heloc for another 6 months, im wondering if it would be worth it to go to a hard money lender?

I’m glad to join this group where I can learn from seasoned investors, and I can help anyone that wants to move or invest in our area.