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1) Yes. It is that simple. just make sure you set the transmit frequency 5 MHz above the receive frequency. Also, initially you may not want to set tone on receive. That way you can hear everything on channel. 2) A repeater sounds like a good solution to your needs. Based on the advertised specifications, the Retevis might be a good candidate. However, I have no personal experience with the radio. As for the antenna, I would want to keep it as simple as possible. If you really are all line of sight to the repeater you will likely get by with a simple quarter wave. Also if the repeater is substantially higher in elevation then the stations that are accessing it, a gain antenna like the J pole might not be a good idea, since they reduce the amount of energy radiated downwards. In this case, the quarter wave would be ideal. Finally, the SamCom does seem to be certified for part 95. The grantee code is 2AIOQ

I'm betting the Retevis with a J-pole will do the job, but you'll want something like a solar charger to avoid killing your car battery. re: SamCom, they sell them as GMRS certified, but I have my doubts...

Yeah, I was eyeing the remote option, and I think I will have to go that route..., I got my hopes up on the semi local ones still having sessions listed.

There are quite a few radio shops in the NYC area. I personally use A&R communications which is in NJ. You can try Barry Electronics 224 W 35th St #408, New York, NY 10001 They sell ham radio and commercial LMR and such

You might want to check with a local Ham Radio club. Many members have various types of antenna measuring equipment and one of them likely would he happy to help check it for you. You may be in for some luck. The last weekend of June is Field Day for Amateur Radio. Many groups, even single operators, setup in local parks, parking lots etc. and operate off of portable/emergency power power. It's a good place to meet other radio minded people and somebody I'm sure has the equipment on site to check your antenna system out. Oh, don't be surprised if somebody suggests getting your Ham License. http://www.arrl.org/field-day

Don't worry about it. Switch to another repeater or use the VFO to find somebody else to talk to. The crappy attitude was at its height around the time the FCC dropped the CW requirement for all license classes. There were endless debates, some still going on, about the merits of dropping or not dropping the CW requirements. Some of the old timers hated that change, and likely will never get over it. I guess they though of it as a some kind of exclusive club. If that was what they valued most then they got into Ham radio for the wrong reason. Go out, make contacts and have fun.