Need advice on metal roof and gutter issues

My house was built in 1983. Previous owner installed a steel (I checked with a magnet) roof over shingles. The metal roof is secured with 2 inch long ring shank nails with rubber washers and 5/16 x 1 1/2 screws with rubber washers around the perimeter. Quite a few of the roofing nails had popped up since I re-set them last year. Is this from expansion and contraction of the metal roof?
After a rain, I see a lot of water droplets coalesce on the bottom of all the gutters and on the front lower edge section of the fascia. On a 22 foot section above my porch I noticed there is no drip edge installed and the soffit is starting to rot. The gutter there is loose and there is a lot of standing water in it. There is hardly any room to get my hands in that section of gutter to clean out debris. The rest of the roof has drip edge installed and the gutters have plenty of room for me the get in there and clean them out. Hardly and standing water there. I'm thinking the water is getting in from the popped up nails and rolling down the roof and getting behind the gutters and/or the water may be overshooting that section of gutter over the porch. As a side note we have lots of pine and maple close to the house so I am frequently cleaning out the gutters. The section with no drip edge has what looks like a long furring strip on the leading edge of the roof over the shingles. Where do I start? Do I take off the gutter completely and rehang it at a better angle?
Can the loose ring shank roofing nails be replaced with longer screws and neoprene washers?
Do I install a gutter apron on the section with no drip edge? If I go with the gutter apron do i have to take out the screws along the edge to slip the apron under the furring strip?

Thanks in advance for your advice! (I don't know why the pictures are sideways!)

 

Hard to say where you should start. Yes, the leaks could be coming from the nails... should never have used nails... unless they hadn't invented screws back then. Replace them with neoprene washer screws (pole barn screws). If that roof was done today, the entire roof would probably have been stripped of the shingles, then would be covered with an ice and water shield barrier over the top of your existing drip edge (and missing drip edge).

Yes, the gutter is going to drip if there is no gutter apron (drip edge) flashing the back side. Looks like they laid the sheet in the bottom pic with the overlap the wrong way. There is probably no bottom foam closure under the roofing at the fascia either. Yes, too long at the gutter... hard to fix that. Cutting it back will work but will burn the finish.

 

Thanks so much for your reply, XSleeper.
Yep, I read quite a few of your posts here on the forum and found that installing a metal roof over shingles was not the right way to go. I live in the rural Tennessee and cutting corners seems to be the norm.
I will start by getting rid of all the nails and install the pole barn screws with neoprene washers.
The nails were 2 inches long. Can I use the Teks #9 x1.5 zinc plated roofing screws or do I need to find a screw at least 2 inches long?

 

The #9 screw will be slightly larger in diameter, so a shorter screw will probably work fine. But I'm pretty sure you could find some brown screws. Got a Menards nearby?

 

Nearest Menards is in the next state…160 miles away! Home depot is about an hour away. We do have a Lowes in town, thats why I mentioned #9 screws because they are in stock there. What would you use? Just give me the specs and I can always order them. Again, I really appreciate the advice.