You'd also need to establish a budget, and secure a master insurance policy. i THINK you need to do these things before reaching out to your municipality to have it converted officially with the county or city but they would be the first ask for steps in order.i will add, this would make financing on these units a bit challenging, as in the mortgage world, at least initially, they would be considered "non-warrantable" condos.

If the numbers make sense, the plan is to approach the seller and attempt to get a lower price for this "2-story" building which has vacancies, since that's what the owner is selling.

While living in a high-cost area can present challenges, it also opens doors to creative strategies, like investing out of state or leveraging partnerships.

Are there any challenges I might face, especially if my long-term tenants aren’t comfortable with the short-term rental activity in the same building?

Challenges?

In Cleveland you can find below market rental ready duplexes that require minor repairs (keep in mind that discounted properties come with their own challenges).

Let’s share our experiences so we can all navigate these challenges more effectively!

By year end I will tackle a MF, value add with my son that would be sweet if we can swing the coop/tic (handling the finance challenges is the hurdle) so he ends up with a unit at below 50% of retail.  

It was all very confusing and challenging because getting free information wasnt as easy as it is now.

Challenges?