questions about taking on a big flipping project as a newbie

[Rachel Feng]

Hi, 

I was originally trying to buy a two-family in a good school district to househack, but the market is too hot now that I do not feel like overpaying those move-in condition properties. Right now I'm exploring the possibility of buying a property that needs more work, flipping it and then converting it to condo. End goal is to sell one of them and occupy the other. To make things easier, let's just use these following two properties currently in the market as an example:

80 Upland Rd, Belmont, MA 02478

35 Trapelo Rd, Belmont, MA 02178

What I am most nervous about is the holding cost. One month of delay would mean another $5000 cost, easily eating in the profit. I'm sure contractors are busy now since market is so hot, so is it possible for me (who does not have any contractor network) to find contractors who can get work done on time, with quality? Other than agents' recommendations, where else can I try to find good contractors? Should I hire a general contractor and let him deal with subcontractors? 

I have not talked to a local bank about construction loans yet, so I am not sure whether it is a cheaper way to do rather than use my own reserves? (assuming I can use the reserves to invest in the stock market instead)

For the properties above, what would be some potential risks to get it done on time? How long is the turnaround for condo conversion application in Belmont or Newton? Are there anything else that I need to keep in mind as a new investor? 

I guess just to prepare for the worst, what could be the potential worst outcome for a new investor to take on a project like this? 

Any insights would be really appreciated!!