I currently own a Ft-250r which is fine for working the local repeaters but I would like to work simplex, however its 5W just doesn't do well for contacts over 10 miles. Should I invest in a new radio (Ft-2900) or should I get a Amp like the Marage B-34?
Be that as it may, I would have gone all the way, grit my teeth, cracked open that wallet and got an FT-857D. Then, be set for almost "DC to daylight" when/if you choose to upgrade to General, or Extra. No other radio has as much to offer for the price. Then, if you choose to upgrade to a "big rig" for your fixed operations, you have a mobile rig all ready to go! Or, dedicate the '857 to all mode 2M/70CM service.
Then, keep the FT-250R for dedicated repeater work. It's also great to have a VHF simplex "back-channel" for quick local stuff while on HF. I and three or four friends do this all the time. It's great if you want to have a quick QSO with a local without interrupting an HF QSO. Later on, maybe, pick up a cheap used 50 or 70 watt VHF amp to "beef up" the back-channel operations.
That's my take and I'm sticking to it.