Condos are cheaper than houses, and to my mind, a vacationer wouldn't care much about staying in a bigger place for their short stay, and would be more concerned with a good location and a nice view.Thoughts?

Set a clear budget, research properties carefully, and keep growth potential in mind as you plan.Good luck!

I mean in general what sort of expert should I try finding first, but if someone has specific people in mind who deal with the UP that works for me too.

You have to start with the end in mind and don't sweat the small stuff and the inevitable inconveniences owning RE will bring. 

I have come to realize I need to use a good and fair contract with a meeting of the minds.

I currently own rentals in Charlotte and Tampa and those were purchased with potential for large appreciation in mind -- not so much cash flow.

My focus is on identifying value-add opportunities and managing properties to maximize cash flow and ROI.I’m here to connect with like-minded investors, share insights, and learn from others in this amazing community.

I just got done making a YT video on the subject, so it's fresh on my mind.

However, keep in mind that tying your primary home to an investment carries inherent risks, especially if the flip doesn't go as planned.

I'd shorten as suggested and include the value to the owner as their mind will quickly go to the pitfalls of this strategy.