Questions about bulking strategy

I am a male, 5’5" and currently 150lbs. Not sure my bodyfat percentage but I have very prominent bicep/Forearm veins, visible veins on my lower abdomen and visible albeit not “chiseled” abs. I’ve been lifting for ~10 years with probably the last 6 or 7 being what I would consider to be pretty good training. Over the last few months I cut down from 170 down to 155 with the goal of getting pretty lean before starting a slow bulk that will hopefully be more successful than my last one, but at the end I had to undergo surgery and lost a further 5lbs quite rapidly as a result.

I’m planning on starting a 250 calorie surplus tomorrow as I begin week 1 of the Bodybuilding 2 template. I expect to gain around 2lbs a month and will adjust calories to stay on course as needed while utilizing Macrofactor for my tracking. My end goal is to be a fairly well muscled 165 as that’s what I think is my highest realistic weight class to compete in. I’d love to be a 181 and feel “big” but getting there seems like it would take multiple years and I’d like to compete sooner than that.

My questions are:

Am I likely to need to over shoot 165 before cutting down and making it my new “walk around” weight in order to be fairly lean at 165?

If I want to be “big” would being 181 at 5’5" likely be feasible if I decide being “lean” isn’t as important to me as being as strong as possible while still maintaining a waist measurement that’s in the healthy range?

I think this is a fine place to start from an energy surplus standpoint. I’m not sure exactly what you mean by “fairly lean” , but you will are unlikely to be as lean as you are now upon going up to 165 initially. Some time in maintenance there and then reassessing what you’d like to do would be reasonable.

Most things are possible, and I suspect being ~181 at your height with a normal waist is one of them. I don’t know enough about you to feel confident one way or another…but seems reasonably likely.

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If upon reaching 165 I find that I have more bodyfat than I’d like would it be advisable to cut again and then do a second bulk? I know 165 is an arbitrary bodyweight but I don’t want to compete too far under the cap for whatever class I end up in, and I’d like to optimize my body composition as best as I’m able to. I’m just not sure if I’d need to eventually bulk beyond 165 in order to cut down to 165 to have my best possible muscle/fat ratio.

I think long term weight management is going to involve multiple bulk and cut cycles along with long periods of maintenance. I would not expect you to achieve your best possible muscle to fat ration immediately upon completing a single bulk .

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Thank you for your responses! Definitely helped clear things up for me.