I just purchased a condo to live in for me and my fiancée recently. It is currently being rehabbed. I don't really regret my decisions on purchasing this place because my fiancée wanted it and we still go it way below market value (even after renovations). However, if I could go back, I would have done a few things differently -
1) I would have chosen a condo with lower HOA fees. The area I will be living in is called Edgewater and I happen to live on a block/street with a bunch of high rise condos where HOA fees are highest (600-800 a month). The location is great in that it is right off of the lake and the balcony opens up to the lake and there are other positives.
However, from an investing standpoint, it may not have been the smartest move. Therefore, to help offset the cost of mortgage and fees, my fiancée and I are considering renting out the second room to house hack. But, if I could go back, I would choose a condo with HOA fees between less than 300 bucks or use a FHA 203k loan to house hack a multifamily unit.
2) I would have contacted the HOA earlier and asked about what was allowed on rehab. Our HOA has many restrictions on what you're allowed to do for rehab.
For example, we weren't allowed to put stationary appliances in front of the baseboard heaters just in case they needed to do repairs on them... which meant that in certain areas of the kitchen, we weren't allow to put appliances there. So, in our situation, we actually had to put wheels on our oven and other floor cabinets so this would not be an issue.
So, if I could go back, I would research HOA rules and regulations thoroughly.
3) I would've negotiated the price of the condo more if I had known that the HOA fees were high since at that time I did not know exactly what was considered high. In retrospect, I think the sellers were extremely motivated and there weren't any offers previously (although they said there were) because of the high HOA fees.
4) I would've had all of the rehab materials and orders in place in order for a smooth and efficient rehab process. I used my dad as a contractor and my fiancée designed the place herself. And since it was going to be our first place together, she wanted it to be perfect! So, the rehab took longer than expected because she did an enormous amount of research. I'm okay with this since it's our own place. But, for future investments, we will have everything ready to go!
Anyways, lesson learned.