Sounds like you've started your research on OOS investing, but the single best piece of advice I can give you is to establish a trusted investor-friendly agent who will be your boots on the ground once you decide which market you want to target.

I have a a great working relationship with the owners in which I maintain the grounds and am credited monthly for my services.

We got out of condo conversions couldn't really sell any of them and transitioned to ground up development of single family homes and three story walkup triplexes on a build to rent model which is much easier for us to manage and our exit isn't a sale it's just a refinance. 

You need boots on the ground (you?)

While my sister and I will not have any issues based on our history and lives, the goal is to use this property as the learning ground for the final outcome: four duplexes---Structuring the property under an LLC or land trust could trigger a due-on-sale clause, so check with the lender before proceeding.

Then, if you are not satisfied with what you find, you can explore other options, but for now, I would find out what is happening on the ground face to face.Best of luck - Chris

Since you’re based in NY, Detroit is just a short flight away, making it feasible to visit and get a feel for the market and the team you’d be working with.That said, I’ve worked with plenty of investors who have never actually visited and still built successful portfolios—it really comes down to having the right boots on the ground.

I invest there and have a full team on-the-ground.

If you don't already have boots-on-the-ground and a trusted network, it's going to be tougher to do.

To get a rough ballpark, sure, but sometimes you'll be way, way off like we've seen with the iBuyers who it turns out were too smart for their own good and ended up buying high and selling low due to to relying on data and not actual organic, boots on the ground experience pulling accurate comps like an appraiser or realtor who knows the market on not just a block by block or street by street but a house by house level.