Thomas Scott, 38, bid on various high-value machines at auction and had them delivered by haulier but never offered payment.
The industrial vehicles - worth more than £10,000 in some cases - would later appear for sale on Ebay.
In one case Scott’s offered to transport a JCB digger worth £16,000 for a Chesterfield farmer which was never seen again.
During another theft the 38-year-old won a bid for a John Deere tractor valued at £7,740 at auction - selling it on for £8,100.
However Scott’s dishonesty crimes were not confined to tractors and excavators - he also resold a £4,200 quad bike won at auction for which he never paid for over £1,000 less.
He made off with a trailer from an Ashbourne sailing club which was never returned and was caught with a stolen Land Rover.
The court heard Scott had 23 convictions for 84 offences including fraud, theft and driving while disqualified.
Recorder David Richards told Scott his dishonesty offences related to farm machinery “generally” - an area of work he was “clearly familiar with”.
The judge said: “You’ve used your familiarity with people in a way as to try and facilitate repeated frauds or thefts of high-value items, causing inconvenience, loss and preying upon trust.
“When you were pressed for payment one excuse followed another and they believed it because they didn’t want to think someone is lying to them.
“When they were dealing with you they were not dealing with someone being straightforward or honest with them.”
The judge said Scott often contacted his victims claiming to be a trader in farm machinery and had all the “trappings” of a legitimate trader.
He added: “You were quite brazen - one of these offenders who front up to people as if to say ‘prove I’m dishonest’.
“You would give reasons as to why funds had not been paid just to get people off your back - then items would appear on Ebay for less than you paid at auction.
“You used various locations to hide the machinery - once you got hold of something it was yours and it didn’t matter that you owed someone for it.”
The court heard when officers arrived at Scott’s home he became “aggressive”, saying “you’ve blown it” while sitting down to use his computer.
After “flailing” his arms about Scott was restrained with cactus spray.
Kelly Cyples, mitigating, said the defendant suffered with depression after suffering the loss of his grandfather.
She said payment was withheld in some cases after arguments over whether VAT should or should not have been added.
The court heard that Scott - already in custody at HMP Nottingham - had saved his cellmate’s life performing CPR for 15 minutes as he was struck down with a heart attack.
Scott, formerly of Lon Y Waen, Menai Bridge, Isle Of Anglesey, admitted fraud, theft, driving while disqualified and resisting arrest.
He was jailed for 47 months and banned from driving for 52 months.