This can be made out to be so complicated and that just scares people off.
The references the original poster made was regarding reception (scratchy signals, ergo poor receiver signal levels). It does not matter if he has an HT, mobile or base station radio. If he is non-line-of-sight and working off of reflected/refracted signals to his antenna then the only things that will help him out are height and system gain.
Poor receive signal levels are never corrected with more transmitter power on your part.
Losses due to feedline are negative gain factors. A good antenna is a positive gain factor.
Any HT on a "duckie" is going to be with a negative gain. Most duckies are on the order of -3 to -6 dBi and with their operating position (next to your head, not vertical, etc...) this is even worse.
If an extra 10' of coax will get you another 10' in the air then whatever feedline losses you encounter are more than offset by an increase in your line-of-sight distances to the radio horizon. There is a practical limit to this; assuming there is no terrain your radio horizon is;
10' height 4 miles
20' height 6 miles
30' height 8 miles
40' height 9 miles
50' height 10 miles
60' height 11 miles
70' height 12 miles
This assumes that the receiving site at the other end is at ground level (0 feet) if they have height then the two radio horizons are added to give a much longer path distance (example, you at 30', the repeater at 50', (8+10=18) 18 miles point to point line-of-sight).http://www.qsl.net/w4sat/horizon.htm
Usually someone is higher up, a repeater mounted on a tower on a hill. All of that needs to be taken into consideration, also any terrain that may be blocking you in the middle (path profiles at VHF/UHF) and other weird things like Fresnel zones, knife edge refraction (do not worry about that now).
Any sort of outdoor antenna at height is better than an HT duckie. Get in the air and get "on" the air.