Selling Condo Rental for Multi-Family Rental?

[Armen G.]

Hello all, this is my first post and I hope it hasn't been addressed before.  My apologies if it has and any links to discussions would be greatly appreciated.  Here is my situation...

My wife and I own a condo (2nd floor unit) that she purchased well before we met. We have a GREAT tenant in it but have been lucky to selectively come across people we know to rent from us. We are finally in the black by $50/month after renting it for 3 years. Recently, the owner of the unit below us flagged some water damage on his ceiling and his neighbor also flagged water damage on his ceiling. In any case, I have filed an insurance claim to address the issues. I want to sell the condo to purchase a multi-family rental (single story). I'm frustrated by the HOA fees disproportionately increasing (long story but the HOA dues are 40% of the monthly mortgage payment due to a poorly structured assessment to the HOA about 15 years ago), frustrated and stressed over the liability of the neighbors from leaks, etc that I have no control over, and generally feeling powerless over so many variables that are not in my control (don't even get me started on how many times I've requested that the roofing over our unit be repaired before the rain arrives). The management company the HOA uses is always unavailable and passing off any responsibilities to the individual tenants. Some of the owners in the building have become more involved in the running of the building but they too feel frustrated by the lack of responsiveness of the management company. I feel that having a multi-family property gives me more control over some of the variables that frustrate me at this point and I'm wondering if this is delusional on my part. Is condo ownership and the collective issues (HOA, tenants below and adjacent, etc) largely different/worse/better than having a standalone structure that I have more control over (to improve, repair, etc)? I don't mind making improvements to my property and fixing issues, especially when I'm not handcuffed to HOA terms. Any advice/stories/insight would be greatly appreciated!!