I'm also a rookie when it comes to Real Estate and in the process of acquiring my first investment property alongside my fiancee in our local region of Cleveland, OH.

There were some hiccups but all in all a smooth transaction, and nothing like that first rent check <3

Does anyone see any potential hiccups with this?

There’s no cushion for cost-overruns, softening in the market (thus a lower sales price and increased DOM), or any other unexpected hiccups that ALWAYS occur.  

Assuming you can build 3 stories with no setback on the third floor (if you're a corner property, if either adjacent house is 3 full stories, or if either lot alongside yours is vacant) you can go 3 stories.

There will always be hiccups along the way and challenges you will face.

The folks at SWBC will come alongside you throughout the renovation process and have a database of contractors they've already vetted and approved.Regarding appraisals, most 203(k) lenders will appraise based on the ARV of the property, so that at least works in your favor :-)Good luck! 

Did the HOA make any changes or were there any other hiccups?

BP is loaded with investors who want funding for their deals, so it's a matter of showing potential investors what you bring to the table but also how much of your net worth is on the hook alongside their capital. 

I know it can be done however I don’t know specifics so if you could detail how you were able to get the property approved and if you had any hiccups, what the solutions were, and you found a good deal, I’d appreciate it!