Real estate investments, when managed wisely, can provide a steady income stream through rental properties, potential tax advantages, and the possibility of significant appreciation in value.To maximize your success, it's essential to conduct thorough research, understand the local market, and seek advice from experienced professionals.

Can you provide any details? 

Construction and heavy reno will create/reveal problems you didn't know existed, have a healthy contingency and stomach.Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I was able to get comps from a friend of mine who’s a real estate agent, but how do I go about finding exactly how much work needs to be done to the home in terms of a dollar amount?

DSTs can provide steady cash flow, tax deferment and will keep pace with inflation as you are still invested in Real Estate, just passively. 

Looking at both short and medium term options and I wanted to see if anyone would be willing to provide any insight on one vs the other. 

In my market they do extremely well with and absolutely provide you with a higher ADR.

Working with fellow realtors/agents or others investors investing out of state on deals & pushing the envelope to compound.

I don't see a home gym as any sort of additional liability, provided that you have machines that are relatively idiot proof and are not inherently dangerous.

Real estate investing provides a wide range of advantages.