Also any tips ? Will I likely need to drill new holes ? Thanks
Yes, you will need to drill new holes.
@Tally Ho gives good advice in his post. I agree with him about filling the old holes and potting new holes. A backing plate is a good idea but you can also use double thickness extra large washers. They will most often be a large improvement over what the building used.
But I have to ask, what are you trying to achieve? If you need more torque for cranking in your sail, are you using a 10" winch handle or 8"? A 10" gives you more torque. The 2" longer handle makes a big difference in the ease of cranking the winch.
Are your 30's single or double speed? If they are single speed, consider upgrading to two speed winches #30s. If you stick with Lewmar the holes may even matchup saving you a lot of work.
Is the main reason for the upgrade to get self tailing winches? And while your doing so, you might as well go bigger?
Remember, bigger isn't always better.
And look at the mounting area. Will the 40s even fit?
My C30 foresail is 283 Sq Ft. It has two speed 40s.
With your C27 having a foresail of 194 Sq Ft, 40's may be a bit of overkill and if so, the added expense and work to install the larger winches may give little payback.
How long will it take me to replace both of them on my Catalina 27?
This a hard question to answer. How fast do you work? Will you have a helper? How is the access to reach the bottom of the winches?
How easy will the old winches come off? Do. you have the right tools? You may need a socket set with several size extensions and a swivel to get to the nuts off?
If I was doing a similar project I'd plan for two days and end up needing three.