How big is the tile-lined flue for the oil burner? How far is it from where the boiler vent enters the flue, to the very top, approximately? (I suspect it's about the right size, if the annual inspection doesn't show any spalling or condensate erosion.)
Having the chimney on an exterior wall, isn't in your favor.
Got a ZIP code (for weather data purposes)?
If on a regular fill-up service, is there a "K-factor" stamped on the billing slips? If yes, what are the K-factors for mid to late winter fill-ups?
The primary factors for flue condensation are the temperature of the flue, the temperature of the exhaust, and the amount of dilution air in the exhaust.
The dew point of the raw oil combustion exhaust is pretty high, since a major component of the combustion product is water. Diluting it with much much drier (in absolute terms) air from the conditioned space lowers dew point of what's going up the flue to more manageable temperature. The dilution air is typically introduced with a barometric damper on the vent piping between the boiler and the chimney, and the amount of that dilution air is somewhat tweakable if you see evidence of condensation happening.
If the chimney is located somewhere in the interior of the house, not on an exterior wall, the flue doesn't need to be heated up as much to be above the dew point of the exhaust, which makes it inherently lower risk than an exterior chimney that cools off quickly between burn cycles. The smaller the cross section of the flue, the less cold surface area is in contact with the exhaust, which means it heats up more quickly, and the higher the stack velocity. Ideally the flue liner would be just barely big enough for the burner size, and not 2x.
The duty cycle of the burner also matters, since the higher the duty cycle, the higher the average temp of the flue liner, which lowers condensation risk. If the boiler output is no more than 1.5x the amount need to cover the heat loss at the 99th percentile outdoor temperature bin (the
99% outside design temperature) the duty cycle would be over 65% whenever it was really cold out. That would usually be enough to keep a terra-cotta lined flue warm enough to avoid major condensation if the flue is right-sized for the burner. But a duty cycle of more than 30-50% isn't very likely (even on the coldest days) unless yours is a very large or very leaky house: The MPO147 has a DOE output of 129,000 BTU/hr which would require an outdoor temp of -180F before it started to lose ground. Even if your heat load is 2x mine, it would still have a duty cycle less than 60%. But if the other risk factors align that's not a big deal. With the K-factor and a ZIP code it's possible to estimate the duty cycle it would be experiencing during the coldest hours of the year.
In my area installing an ~87% AFUE oil boiler without a right-sized stainless flue liner would be a code violation. It's not a cheap solution, but it solves a lot of issues: By right-sizing the flue the stack velocity is maximized, and the thermal mass of stainless steel is a fraction that of terra cotta liners, so it heats up very quickly during a burn cycle. Both the high stack velocity and low thermal mass minimizes flue condensation risk, but more importantly, (nearly) completely mitigates damage to the integrity of the chimney when condensation does occur, since it is condensing on stainless steel, which can handle the high acidity rather than soaking into terra cotta and mortar, both of which become degrade by the acidity.