The most important considerations are what the lot is zoned for, what the minimum lot size is, what size houses you could then build on those lots, and having street access for all the lots. Then you have issues of meeting setback, sideyard, etc. reqts for all the lots. If it turns out all this is OK, then it should be pretty straightforward.
If you can't meet all the requirements, then to split the property, you will need a variance. And that's up to the local Board of Adustment, or similar body. Whether they grant it depends on how extreme the variance deviates from zoning, whether it's some type of hardship case, if the neighbors support the idea or object, who you know, and what mood the board is in. If you need to go this route, the cost will be much higher, win or lose, because they typically want more site plans, info, you may need expert witnesses, etc.
As others have suggested, find out from the city what it's zoned for and the various requirements for that zone. You can do a first pass on your own to figure out if there are any immediate show stoppers without spending any money, except maybe to buy a copy of the zoning book.