Brrrr, Househacking, and taxes Oh my

[David Roberts]

Hi BP, I'm an aspiring REI from Columbus, OH preparing to make my first deal and this is my first post :) I've owner occupied a SFH in a high-appreciating neighborhood of Columbus for the last 6 years (Clintonville). I'm ready to turn this property over and use those profits to start investing in buy/holds in and around Columbus. I've identified House-hacking a multi family building up to 4 units that needs some rehab with FHA financing to be an ideal first move for me, but am also considering cash purchase of a Multi or SFH to do a live-in rehab which I would later refi and rent out. In all 3 strategies I have the same question for those of you who have done this before - and it's related to taxes: ...are there any rehab timeline strategies you employ to best leverage your tax responsibilities in these types of deals? Are there any repairs/improvements that it would make sense to complete AFTER you have a tenant/lease in place? General example: Placing first tenant in December, but waiting until March to install or service the AC unit. That kind of thing... -David