Should I pull the trigger on this trip???

[Josh Silvester]

Hi everyone, my names Josh and I am looking to get into my first property by house hacking. Obviously the market is tricky at the moment but I am in deep thought about a triplex in my area. I would be offering about 25-30k over asking to stay competitive with other buyers. In the first year of living there, my expenses would be breaking even from what I currently pay in rent (about 1400). After a year of living there I could rent out the additional unit along with the other 2 to cash flow only about $50-100/month. I am afraid that my margins are way too tight on this property but at the same time I’m hopeful interest rates will continue to go down so I can refinance and cash flow substantially more ($700-1000 with increased rents and refinancing). 

My question is, should I put in the “overpay” offer for this triplex knowing that they are extremely hard to come by and I won’t be legitimately cash flowing for at least a year maybe 2. Or wait for something else? 

Also worth noting, I am setting aside $450/mn in Cap X because this property will need a new roof within 5 years. Without this added expense my numbers would obviously be much better with this market.