I am in the research phase of building a bike from the ground up. I am looking for some guidance on where to start and what to look out for. So I would like to hear your thoughts.

This will be a bobber style build with a fat from and rear tire. I would like to keep the bike as stripped down as possible with very minimal wiring. I am definitely thinking hardtail but not 100%.

Do I try and find a used roller and if so what model? Or do I go with a custom frame and which company?

For the motor, should I stay with a modern motor or an old school motor. I would love to bring new life into an old motor. Is there one you would recommend or say to stay away from?

Thanks for the help.

 

For the motor, I would recommend a carbureted Harley evo. they can be had cheaper than others, and there are plenty of parts for them. With the right cam and ignition they will perform well. Plus they have the classic Harley sound that you can't get with the twin cam. Essentially the evo is just an improved shovel. (blasphemy!)
Stay away from fuel injection unless you want to deal with a whole lot more electronics. I build one... will never do it again.

Frame wise, a rigid is much cheaper, but after almost a decade of riding them I have to say; if you plan on riding hundreds of miles you will be very tired... and your back will hurt! It's a blast, you really learn to read the road, but you feel every crack and bump. If your just planning daily rides, just around town or so, the rigid is as hardcore as you can get, and depending on the roads where you live, it's not too bad.
A softail frame will cost more, but smooth out the road.

I would suggest you spend a good amount of time on the internet researching the bike you want and the prices of the parts you'll need. I've relied on ebay for most of my purchases, trying to be carful and not wind up with crap. It's a gamble that has paid off for me in the long run.

 

This really depends on Your skill set. My bike is a 74 FXE (superglide) That I have heavily modified. It is the original frame cut and welded to be a softtail.
almost everything is handmade.