Piecing the broken Ibrox outfit back together has proved a costly business, with the club having tallied up more than £80million in losses since re-emerging from its 2012 financial meltdown.
The ramifications of that rebuilding project continue to live on, with Rangers chiefs admitting last year they would need to raise another £20million by the end of next season just to keep the lights on.
But Bennett hopes the days of the club going cap in hand to investors will soon be over after seeing Steven Gerrard's team romp to Rangers' 55th league title.
Gers now have a string of high-value assets with the likes of Alfredo Morelos, Ryan Kent, Borna Barisic and Glen Kamara. At least one of those key men will likely be sold this summer to balance the books but a return to the group stages of the Champions League next season could also provide a £30million windfall.
And Bennett hopes that will be enough to ensure the Light Blues never again slip back into the red.
"In the accounts we made it clear about the funding needs and deficit going forward and how we planned to meet that. That has been through the investors and remains the investors.
"The deficit we did have is coming down. It's been our job to do what we've done - deliver 55, go toe-to-toe with top teams in Europe - but do so while heading towards sustainability.
"Transfer windows will have really big part to play in that,” he told the Louden Tavern podcast. "But if I see the rate we've whittled down the financial deficit, which is still meaningful, then within the next 12 to 18 months - and we need things to go our way - I think we're looking at financial self-sustainability."
Rangers have secured several million pounds worth of fresh cash over the last year, with Far East businessman Stuart Gibson and US tycoon John Halstead joining a group of wealthy investors who have helped to prop up the club and Bennett insists the club will never again return to the boom and bust days of the David Murray era.
But that does not mean Gerrard will be forced to sell off his top stars to the first bidder either.
"No club should run on financial deficit after financial deficit - least of all this club, which has been kicked from pillar to post in so many ways in the last decade," he said.
"We mustn't ever again go to a level of overreach where we jeopardise this club. Never again.
"We think we can achieve every success we want to achieve at home and in Europe within the bandwidth of a sustainable model.
"So when I talk about player trading, it doesn't mean you sell at prices that are undesirable, don't meet your valuation and don't meet the medium and long-term plan.
"This is very well thought out - no fire sales but planned player trading. We're on the cusp of that."