I really sympathize with your efforts; you are trying to study despite of pretty difficult situation and tough schedules.
I would like to give you just a few ideas.
First of all, you can do a lot of development and study without your own Web site. As you mentioned "go to back end and upload files", you certainly do have some Web site; maybe the key is "my own". And I would not advise to get your own hosting, at least not until you develop some product or site you really need to use; this way, you can avoid wasting money. So, my points are: 1) you really need to have your own Web server for development; 2) a lot of work can be done without any site and Web server at all.
Having your own server is much easier than many beginners think. What you need depends on what you want to achieve, but, in particular, Apache is open-source, extremely light-weight and installs in few minutes without problems. Once installed, it can be executed locally. The other steps depends on what server-side technology you want to have. There are some other light-weight HTTP servers you can use. If you use the HTTP server and the site on your development machine, you don't really "deploy" anything, you simply edit the files in place. It's important to use some decent Revision Control system, which also can be extremely light-weight and reliable.
Now, as to the designs with different fonts and preview of the designs, the whole idea of up-loading of some files to the server is methodologically wrong. Not only for your font-related purposes, but for design itself, I would strongly recommend to develop Web page design prototypes locally, fully on the client side. A Web browser along is a decent platform which has all you need: HTML/XHTML, CSS and JavaScript. This is more than enough to prototype any design. Even though it may seem double work, because with server side your scripts are generated by some server-side script, so you cannot re-use the code, prototyping is never the waste of time. With such a problem is general design and font selection, it should be just obvious, but it remains true even for the pages using complicated server-side scripting. One important aspect is: this way, you can better learn what really happens. On this site, we observe too many "developers" trying to achieve quite complicated behavior but having no clue what really happens on server and client side.
Finally, one case where you can do client-side and server-side development altogether in place: ASP.NET development with Visual Studio. These days, you can use fully-functional Community Edition, which is free of charge; its functionality roughly matches "Professional" version. With this approach, you automatically use a tiny "development HTTP server", so you can immediately edit and test server-side and client-side code at the same time.
Again, my answer is much broader than your little font issue, which does not require most of the features discussed above. But you want to study all the development, right? You can do it all locally and efficiently.
—SA
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