SamTiing,
First thing you should do is purchase the HD service manual for your model/year. Search on Ebay, some decent deals to be had there. I would tell you that any early SM, say '99-'02 but '99 was was the first year of the Twin Cam and later manuals won't have some of the same information due to changes that were made. Do an internet search for HD Service Bulletin M1097 as it pertains specifically to the '99 model year.
The very first '99s came with rear cams that attached and indexed to the sprockets using a Woodruff key. A running change modified this attachment to an indexed spline arrangement. The '99 cams were supported with ball bearings in the cam plate. Due to failures, another running change was made and the rear outer cam bearing was changed to a roller bearing with the inner race pressed onto the cam's outer shaft. This is what M1097 talks about. If you have the keyed cams I do not know if the roller bearing will work. It was designed to work with the splined cams.
If you have a 99 and are using ANY other cam plate than the one that originally came with the bike there is an oil supply hole that must be blocked with a screw identified in the linked Andrews document on the last page.
http://www.andrewsproducts.com/files/assets/Cams_conversion_chain-01.pdf
If are replacing the cams and/or possibly a new sprocket pay attention to the 180° ridge made into it. That is to operate the cam position sensor used in 99-01 models. The below link identifies roller chain version that can be used with some later modifications:
https://www.denniskirk.com/andrews/roller-conversion-cam-sprocket-216015.p140050.prd/140050.sku
If you need to get a splined sprocket, a roller chain sprocket (above) or go with gear cams the respective sprocket/gear needs to have this feature. Some folks don't know this and have installed sprockets without this and had issues.
Now, if all this makes you regret getting a '99 model, no worries; that model year has the strongest bottomee and assembly's of all the twin cams.
JMHO but a cam chest upgrade would be a good idea and if you have basic mechanical skills, a decent set o hand tools, torque wrenches and the service manual, the upgrades are truly a DIY project. There are a couple of "special" tools referred to in the SM but there are work arounds for those. However, if you have access to a dependable, knowledgeable independent tech, you shouldn't have to pay for more than 8 hours at the shop rate; most in my area run $75-$100 an hour. A good tech could do this in 4 hours if all the parts are on hand and no surprises.
JMHO but at 10K miles everything in the cam chest should be within service limits so the upgrades that follow are those IMHO necessary to insure the longevity of the motor. Again, JMHO but the OEM cam chest is fairly robust and can remain serviceable for a long time with a few upgrades and you can save yourself a wad of $$ by avoiding gear drive cams, new cam plate and the hydro/roller conversion.
Retain the OEM cam plate
Retain OEM pushrods and tubes
Replace the tensioners with a set off CYCO tensioners
Replace the inner cam bearings with Torrington/Toyo B148s
Replace the outer cam bearings and upgrade the rear outer bearing to a roller.
If you want a performance boost, replace the OEM cams with a set of S&S 509 cams
Replace the OEM oil pressure relief spring with the Baisley LMR-002 for consistent low RPM oil pressure
I hope the bike is carbed and if it is, you will likely need to re-jet if you upgrade the cam set. If the bike is EFI, the system is the Magneti Marelli system which is a whole separate can of worms and difficult to find tuners that are familiar with that system.
Good luck!
