If your file and its metadata creating one resource, its perfectly fine to upload them both in one request. Sample request would be :
POST https://target.com/myresources/resourcename HTTP/1.1
Accept: application/json
Content-Type: multipart/form-data;
boundary=-----------------------------28947758029299
Host: target.com
-------------------------------28947758029299
Content-Disposition: form-data; name="application/json"
{"markers": [
{
"point":new GLatLng(40.266044,-74.718479),
"homeTeam":"Lawrence Library",
"awayTeam":"LUGip",
"markerImage":"images/red.png",
"information": "Linux users group meets second Wednesday of each month.",
"fixture":"Wednesday 7pm",
"capacity":"",
"previousScore":""
},
{
"point":new GLatLng(40.211600,-74.695702),
"homeTeam":"Hamilton Library",
"awayTeam":"LUGip HW SIG",
"markerImage":"images/white.png",
"information": "Linux users can meet the first Tuesday of the month to work out harward and configuration issues.",
"fixture":"Tuesday 7pm",
"capacity":"",
"tv":""
},
{
"point":new GLatLng(40.294535,-74.682012),
"homeTeam":"Applebees",
"awayTeam":"After LUPip Mtg Spot",
"markerImage":"images/newcastle.png",
"information": "Some of us go there after the main LUGip meeting, drink brews, and talk.",
"fixture":"Wednesday whenever",
"capacity":"2 to 4 pints",
"tv":""
},
] }
-------------------------------28947758029299
Content-Disposition: form-data; name="name"; filename="myfilename.pdf"
Content-Type: application/octet-stream
%PDF-1.4
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)%[email protected]
[
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<</Type/Page/MediaBox[0 0 595 842]/Resources<</Font<</F1 1 0 R>>>>/Contents 2 0 R/Parent 3 0 R>>
endobj
1 0 obj
<</Type/Font/Subtype/Type1/BaseFont/Helvetica/Encoding/WinAnsiEncoding>>
endobj
3 0 obj
<</Type/Pages/Count 1/Kids[4 0 R]>>
endobj
5 0 obj
<</Type/Catalog/Pages 3 0 R>>
endobj
6 0 obj
<</Producer(iTextSharp 5.5.11 2000-2017 iText Group NV \(AGPL-version\))/CreationDate(D:20170630120636+02'00')/ModDate(D:20170630120636+02'00')>>
endobj
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-------------------------------28947758029299--